Use Of Thienopyrimidines

EXAMPLE 1

3.02 g of 3,4-methylenedioxybenzylamine (“A”) are added to a solution of 3.29 g of 2,4-dichloro-6-methylthieno[2,3-d]pyrimidine in 80 ml of dichloromethane, 1.52 g of triethylamine are added, and the mixture is stirred at room temperature for 12 hours. The solvent is removed and subjected to conventional work-up, giving 3.38 g of 2-chloro-6-methyl-4-(3,4-methylene-dioxybenzylamino)thieno[2,3-d]pyrimidine, m.p. 162°.

Analogous Reaction of “A”

with 2,4-dichloro-5-methylthieno[2,3-d]pyrimidine gives 2-chloro-5-methyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]-pyrimidine;

with 2,4-dichloro-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-chloro-5,6,7,8-tetrahydro-4-(3,4-methylenedioxybenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine, m.p. 222°;

with 2,4-dichloro-5,6-cyclopenteno-[1]-benzylthieno[2,3-d]pyrimidine gives 2-chloro-5,6-cyclopenteno-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-5,6-cyclohepteno-[1]-benzylthieno[2,3-d]pyrimidine gives 2-chloro-5,6-cyclohepteno-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-6-ethylthieno[2,3-d]pyrimidine gives 2-chloro-6-ethyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine, m.p. 148°;

with 2,4,6-trichlorothieno[2,3-d]pyrimidine gives 2,6-dichloro-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;

with 2,4,5-trichloro-6-methylthieno[2,3-d]pyrimidine gives 2,5-dichloro-6-methyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-6-nitrothieno[2,3-d]pyrimidine gives 2-chloro-6-nitro-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-chloro-5,6-dimethyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-chloro-6-trifluoromethyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine.

Analogous Reaction of 3-chloro-4-methoxybenzylamine

with 2,4-dichloro-6-methylthieno[2,3-d]pyrimidine gives 2-chloro-6-methyl-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]-pyrimidine;

with 2,4-dichloro-5-methylthieno[2,3-d]pyrimidine gives 2-chloro-5-methyl-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]-pyrimidine;

with 2,4-dichloro-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-chloro-5,6,7,8-tetrahydro-4-(3-chloro-4-methoxybenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine;

with 2,4-dichloro-5,6-cyclopenteno-[1]-benzylthieno[2,3-d]pyrimidine gives 2-chloro-5,6-cyclopenteno-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-5,6-cyclohepteno-[1]-benzylthieno[2,3-d]pyrimidine gives 2-chloro-5,6-cyclohepteno-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-6-ethylthieno[2,3-d]pyrimidine gives 2-chloro-6-ethyl-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;

with 2,4,6-trichlorothieno[2,3-d]pyrimidine gives 2,6-dichloro-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;

with 2,4,5-trichloro-6-methylthieno[2,3-d]pyrimidine gives 2,5-dichloro-6-methyl-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-6-nitrothieno[2,3-d]pyrimidine gives 2-chloro-6-nitro-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-chloro-5,6-dimethyl-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-chloro-6-trifluoromethyl-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine.

Analogous Reaction of 3,4-dimethoxybenzylamine

with 2,4-dichloro-6-methylthieno[2,3-d]pyrimidine gives 2-chloro-6-methyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]-pyrimidine;

with 2,4-dichloro-5-methylthieno[2,3-d]pyrimidine gives 2-chloro-5-methyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-5,6,7,8-tetrahydro-[1]-[1]-benzylthieno[2,3-d]pyrimidine gives 2-chloro-5,6,7,8-tetrahydro-4-(3,4-dimethoxybenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine;

with 2,4-dichloro-5,6-cyclopenteno-[1]-benzylthieno[2,3-d]pyrimidine gives 2-chloro-5,6-cyclopenteno-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-5,6-cyclohepteno-[1]-benzylthieno[2,3-d]pyrimidine gives 2-chloro-5,6-cyclohepteno-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-6-ethylthieno[2,3-d]pyrimidine gives 2-chloro-6-ethyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;

with 2,4,6-trichlorothieno[2,3-d]pyrimidine gives 2,6-dichloro-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;

with 2,4,5-trichloro-6-methylthieno[2,3-d]pyrimidine gives 2,5-dichloro-6-methyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-6-nitrothieno[2,3-d]pyrimidine gives 2-chloro-6-nitro-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-chloro-5,6-dimethyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-chloro-6-trifluoromethyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]-pyrimidine.

Analogous Reaction of benzylamine

with 2,4-dichloro-6-methylthieno[2,3-d]pyrimidine gives 2-chloro-6-methyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]-pyrimidine;

with 2,4-dichloro-5-methylthieno[2,3-d]pyrimidine gives 2-chloro-5-methyl-4-benzylaminothieno[2,3-d]pyrimidine;

with 2,4-dichloro-5,6,7,8-tetrahydro-[1]-[1]-benzylthieno[2,3-d]pyrimidine gives 2-chloro-5,6,7,8-tetrahydro-4-benzylamino-[1]-benzylthieno[2,3-d]-pyrimidine;

with 2,4-dichloro-5,6-cyclopenteno-[1]-benzylthieno[2,3-d]pyrimidine gives 2-chloro-5,6-cyclopenteno-4-benzylaminothieno[2,3-d]pyrimidine;

with 2,4-dichloro-5,6-cyclohepteno-[1]-benzylthieno[2,3-d]pyrimidine gives 2-chloro-5,6-cyclohepteno-4-benzylaminothieno[2,3-d]pyrimidine;

with 2,4-dichloro-6-ethylthieno[2,3-d]pyrimidine gives 2-chloro-6-ethyl-4-benzylaminothieno[2,3-d]pyrimidine;

with 2,4,6-trichlorothieno[2,3-d]pyrimidine gives 2,6-dichloro-4-benzylaminothieno[2,3-d]pyrimidine;

with 2,4,5-trichloro-6-methylthieno[2,3-d]pyrimidine gives 2,5-dichloro-6-methyl-4-benzylaminothieno[2,3-d]pyrimidine;

with 2,4-dichloro-6-nitrothieno[2,3-d]pyrimidine gives 2-chloro-6-nitro-4-benzylaminothieno[2,3-d]pyrimidine;

with 2,4-dichloro-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-chloro-5,6-dimethyl-4-benzylaminothieno[2,3-d]pyrimidine;

with 2,4-dichloro-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-chloro-6-trifluoromethyl-4-benzylaminothieno[2,3-d]pyrimidine.

Analogous Reaction of 4-fluorobenzylamine

with 2,4-dichloro-6-methylthieno[2,3-d]pyrimidine gives 2-chloro-6-methyl-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-5-methylthieno[2,3-d]pyrimidine gives 2-chloro-5-methyl-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-chloro-5,6,7,8-tetrahydro-4-(4-fluorobenzylamino)-[1]-benzylthieno-[2,3-d]pyrimidine;

with 2,4-dichloro-5,6-cyclopenteno-[1]-benzylthieno[2,3-d]pyrimidine gives 2-chloro-5,6-cyclopenteno-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-5,6-cyclohepteno-[1]-benzylthieno[2,3-d]pyrimidine gives 2-chloro-5,6-cyclohepteno-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-6-ethylthieno[2,3-d]pyrimidine gives 2-chloro-6-ethyl-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;

with 2,4,6-trichlorothieno[2,3-d]pyrimidine gives 2,6-dichloro-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;

with 2,4,5-trichloro-6-methylthieno[2,3-d]pyrimidine gives 2,5-dichloro-6-methyl-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-6-nitrothieno[2,3-d]pyrimidine gives 2-chloro-6-nitro-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-chloro-5,6-dimethyl-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-chloro-6-trifluoromethyl-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine.

Analogous Reaction of 3,4-dichlorobenzylamine

with 2,4-dichloro-6-methylthieno[2,3-d]pyrimidine gives 2-chloro-6-methyl-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-5-methylthieno[2,3-d]pyrimidine gives 2-chloro-5-methyl-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-chloro-5,6,7,8-tetrahydro-4-(3,4-dichlorobenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine;

with 2,4-dichloro-5,6-cyclopenteno-[1]-benzylthieno[2,3-d]pyrimidine gives 2-chloro-5,6-cyclopenteno-4-(3,4-dichlorobenzylamino)thieno[2,3-d]-pyrimidine;

with 2,4-dichloro-5,6-cyclohepteno-[1]-benzylthieno[2,3-d]pyrimidine gives 2-chloro-5,6-cyclohepteno-4-(3,4-dichlorobenzylamino)thieno[2,3-d]-pyrimidine;

with 2,4-dichloro-6-ethylthieno[2,3-d]pyrimidine gives 2-chloro-6-ethyl-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;

with 2,4,6-trichlorothieno[2,3-d]pyrimidine gives 2,6-dichloro-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;

with 2,4,5-trichloro-6-methylthieno[2,3-d]pyrimidine gives 2,5-dichloro-6-methyl-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-6-nitrothieno[2,3-d]pyrimidine gives 2-chloro-6-nitro-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-chloro-5,6-dimethyl-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-chloro-6-trifluoromethyl-4-(3,4-dichlorobenzylamino)thieno[2,3-d]-pyrimidine.

Analogous Reaction of 3-nitrobenzylamine

with 2,4-dichloro-6-methylthieno[2,3-d]pyrimidine gives 2-chloro-6-methyl-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-5-methylthieno[2,3-d]pyrimidine gives 2-chloro-5-methyl-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-chloro-5,6,7,8-tetrahydro-4-(3-nitrobenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine;

with 2,4-dichloro-5,6-cyclopenteno-[1]-benzylthieno[2,3-d]pyrimidine gives 2-chloro-5,6-cyclopenteno-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-5,6-cyclohepteno-[1]-benzylthieno[2,3-d]pyrimidine gives 2-chloro-5,6-cyclohepteno-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-6-ethylthieno[2,3-d]pyrimidine gives 2-chloro-6-ethyl-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;

with 2,4,6-trichlorothieno[2,3-d]pyrimidine gives 2,6-dichloro-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;

with 2,4,5-trichloro-6-methylthieno[2,3-d]pyrimidine gives 2,5-dichloro-6-methyl-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-6-nitrothieno[2,3-d]pyrimidine gives 2-chloro-6-nitro-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-chloro-5,6-dimethyl-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-chloro-6-trifluoromethyl-4-(3-nitrobenzylamino)thieno[2,3-d]-pyrimidine.

Analogous Reaction of 3,4-methylenedioxyphenethylamine

with 2,4-dichloro-6-methylthieno[2,3-d]pyrimidine gives 2-chloro-6-methyl-4-(3,4-methylenephenethylamino)thieno[2,3-d]-pyrimidine;

with 2,4-dichloro-5-methylthieno[2,3-d]pyrimidine gives 2-chloro-5-methyl-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-chloro-5,6,7,8-tetrahydro-4-(3,4-methylenedioxyphenethylamino)-[1]-benzylthieno[2,3-d]pyrimidine;

with 2,4-dichloro-5,6-cyclopenteno-[1]-benzylthieno[2,3-d]pyrimidine gives 2-chloro-5,6-cyclopenteno-4-(3,4-methylenedioxyphenethylamino)-thieno[2,3-d]pyrimidine;

with 2,4-dichloro-5,6-cyclohepteno-[1]-benzylthieno[2,3-d]pyrimidine gives 2-chloro-5,6-cyclohepteno-4-(3,4-methylenedioxyphenethylamino)-thieno[2,3-d]pyrimidine;

with 2,4-dichloro-6-ethylthieno[2,3-d]pyrimidine gives 2-chloro-6-ethyl-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]-pyrimidine;

with 2,4,6-trichlorothieno[2,3-d]pyrimidine gives 2,6-dichloro-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;

with 2,4,5-trichloro-6-methylthieno[2,3-d]pyrimidine gives 2,5-dichloro-6-methyl-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-6-nitrothieno[2,3-d]pyrimidine gives 2-chloro-6-nitro-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]-pyrimidine;

with 2,4-dichloro-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-chloro-5,6-dimethyl-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-chloro-6-trifluoromethyl-4-(3,4-methylenedioxyphenethylamino)-thieno[2,3-d]pyrimidine.

Analogous Reaction of 3,4-ethylenedioxybenzylamine

with 2,4-dichloro-6-methylthieno[2,3-d]pyrimidine gives 2-chloro-6-methyl-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]-pyrimidine;

with 2,4-dichloro-5-methylthieno[2,3-d]pyrimidine gives 2-chloro-5-methyl-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-chloro-5,6,7,8-tetrahydro-4-(3,4-ethylenedioxybenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine;

with 2,4-dichloro-5,6-cyclopenteno-[1]-benzylthieno[2,3-d]pyrimidine gives 2-chloro-5,6-cyclopenteno-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-5,6-cyclohepteno-[1]-benzylthieno[2,3-d]pyrimidine gives 2-chloro-5,6-cyclohepteno-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-6-ethylthieno[2,3-d]pyrimidine gives 2-chloro-6-ethyl-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;

with 2,4,6-trichlorothieno[2,3-d]pyrimidine gives 2,6-dichloro-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;

with 2,4,5-trichloro-6-methylthieno[2,3-d]pyrimidine gives 2,5-dichloro-6-methyl-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]-pyrimidine;

with 2,4-dichloro-6-nitrothieno[2,3-d]pyrimidine gives 2-chloro-6-nitro-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;

with 2,4-dichloro-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-chloro-5,6-dimethyl-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]-pyrimidine;

with 2,4-dichloro-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-chloro-6-trifluoromethyl-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine.

EXAMPLE 2

1.67 g of 2-chloro-6-methyl-4-(3,4-methylenedioxybenzylamino)thieno-[2,3-d]pyrimidine, 1.02 g of imidazole and 2 g of phenol are heated at 150° for 5 hours. After cooling, the residue is dissolved in dichloromethane and subjected to conventional work-up, giving 1.0 g of 2-(imidazol-1-yl)-6-methyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine, m.p. 248-250°.

Analogous reaction of imidazole with the 4-arylalkylamino-substituted 2-chlorothieno[2,3-d]pyrimidine derivatives obtained under Example 1 gives the following compounds

2-(imidazol-1-yl)-5-methyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine, m.p. 238°;
2-(imidazol-1-yl)-5,6,7,8-tetrahydro-4-(3,4-methylenedioxybenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine, m.p. 218°;
2-(imidazol-1-yl)-5,6-cyclopenteno-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine, m.p. 260°;
2-(imidazol-1-yl)-5,6-cyclohepteno-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine, m.p. 210°;
2-(imidazol-1-yl)-6-ethyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine, methanesulfonate, m.p. 201°;
2-(imidazol-1-yl)-6-chloro-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5-chloro-6-methyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-nitro-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6-dimethyl-4-(3,4-methylenedioxybenzylamino)-thieno[2,3-d]pyrimidine, m.p. 245°
2-(imidazol-1-yl)-6-trifluoromethyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-methyl-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5-methyl-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6,7,8-tetrahydro-4-(3-chloro-4-methoxybenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6-cyclopenteno-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6-cyclohepteno-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-ethyl-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-chloro-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5-chloro-6-methyl-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-nitro-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6-dimethyl-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-trifluoromethyl-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-methyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5-methyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6,7,8-tetrahydro-4-(3,4-dimethoxybenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6-cyclopenteno-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6-cyclohepteno-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-ethyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]-pyrimidine;
2-(imidazol-1-yl)-6-chloro-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]-pyrimidine;
2-(imidazol-1-yl)-5-chloro-6-methyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-nitro-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]-pyrimidine;
2-(imidazol-1-yl)-5,6-dimethyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-trifluoromethyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-methyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-methyl-4-benzylaminothieno[2,3-d]pyrimidine, m.p. 207°;
2-(imidazol-1-yl)-5-methyl-4-benzylaminothieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6,7,8-tetrahydro-4-benzylamino-[1]-benzylthieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6-cyclopenteno-4-benzylaminothieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6-cyclohepteno-4-benzylaminothieno[2,3-d]pyrimidine, m.p. 197°;
2-(imidazol-1-yl)-6-ethyl-4-benzylaminothieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-chloro-4-benzylaminothieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5-chloro-6-methyl-4-benzylaminothieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-nitro-4-benzylaminothieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6-dimethyl-4-benzylaminothieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-trifluoromethyl-4-benzylaminothieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-methyl-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5-methyl-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6,7,8-tetrahydro-4-(4-fluorobenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6-cyclopenteno-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6-cyclohepteno-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-ethyl-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine, m.p. 199°;
2-(imidazol-1-yl)-6-chloro-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5-chloro-6-methyl-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-nitro-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6-dimethyl-4-(4-fluorobenzylamino)thieno[2,3-d]-pyrimidine;
2-(imidazol-1-yl)-6-trifluoromethyl-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-methyl-4-(3,4-dichlorobenzylamino)thieno[2,3-d]-pyrimidine;
2-(imidazol-1-yl)-5-methyl-4-(3,4-dichlorobenzylamino)thieno[2,3-d]-pyrimidine;
2-(imidazol-1-yl)-5,6,7,8-tetrahydro-4-(3,4-dichlorobenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6-cyclopenteno-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6-cyclohepteno-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-ethyl-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-chloro-4-(3,4-dichlorobenzylamino)thieno[2,3-d]-pyrimidine;
2-(imidazol-1-yl)-5-chloro-6-methyl-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-nitro-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6-dimethyl-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-trifluoromethyl-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-methyl-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5-methyl-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6,7,8-tetrahydro-4-(3-nitrobenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6-cyclopenteno-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6-cyclohepteno-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-ethyl-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-chloro-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5-chloro-6-methyl-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-nitro-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6-dimethyl-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-trifluoromethyl-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-methyl-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5-methyl-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6,7,8-tetrahydro-4-(3,4-methylenedioxyphenethylamino)-[1]-benzylthieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6-cyclopenteno-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6-cyclohepteno-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-ethyl-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-chloro-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5-chloro-6-methyl-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-nitro-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6-dimethyl-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-trifluoromethyl-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine.
2-(imidazol-1-yl)-6-methyl-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5-methyl-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6,7,8-tetrahydro-4-(3,4-ethylenedioxybenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6-cyclopenteno-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6-cyclohepteno-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-ethyl-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-chloro-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5-chloro-6-methyl-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-nitro-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-5,6-dimethyl-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(imidazol-1-yl)-6-trifluoromethyl-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine.

Analogous reaction of pyrazole with the 4-arylalkylamino-substituted 2-chlorothieno[2,3-d]pyrimidine derivatives obtained under Example 1 gives the following compounds

2-(pyrazol-1-yl)-5-methyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6,7,8-tetrahydro-4-(3,4-methylenedioxybenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine, m.p. 210°;
2-(pyrazol-1-yl)-5,6-cyclopenteno-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6-cyclohepteno-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-ethyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-chloro-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5-chloro-6-methyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-nitro-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6-dimethyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-trifluoromethyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-methyl-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5-methyl-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6,7,8-tetrahydro-4-(3-chloro-4-methoxybenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6-cyclopenteno-4-(3-chloro-4-methyoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6-cyclohepteno-4-(3-chloro-4-methyoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-ethyl-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-chloro-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5-chloro-6-methyl-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-nitro-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6-dimethyl-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-trifluoromethyl-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-methyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]-pyrimidine;
2-(pyrazol-1-yl)-5-methyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]-pyrimidine;
2-(pyrazol-1-yl)-5,6,7,8-tetrahydro-4-(3,4-dimethoxybenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6-cyclopenteno-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6-cyclohepteno-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-ethyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]-pyrimidine;
2-(pyrazol-1-yl)-6-chloro-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]-pyrimidine;
2-(pyrazol-1-yl)-5-chloro-6-methyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-nitro-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]-pyrimidine;
2-(pyrazol-1-yl)-5,6-dimethyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-trifluoromethyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-methyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]-pyrimidine;
2-(pyrazol-1-yl)-5-methyl-4-benzylaminothieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6,7,8-tetrahydro-4-benzylamino-[1]-benzylthieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6-cyclopenteno-4-benzylaminothieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6-cyclohepteno-4-benzylaminothieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-ethyl-4-benzylaminothieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-chloro-4-benzylaminothieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5-chloro-6-methyl-4-benzylaminothieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-nitro-4-benzylaminothieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6-dimethyl-4-benzylaminothieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-trifluoromethyl-4-benzylaminothieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-methyl-4-(4-fluorobenzylamino)thieno[2,3-d]-pyrimidine;
2-(pyrazol-1-yl)-5-methyl-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6,7,8-tetrahydro-4-(4-fluorobenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6-cyclopenteno-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6-cyclohepteno-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-ethyl-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-chloro-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5-chloro-6-methyl-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-nitro-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6-dimethyl-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-trifluoromethyl-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-methyl-4-(3,4-dichlorobenzylamino)thieno[2,3-d]-pyrimidine;
2-(pyrazol-1-yl)-5-methyl-4-(3,4-dichlorobenzylamino)thieno[2,3-d]-pyrimidine;
2-(pyrazol-1-yl)-5,6,7,8-tetrahydro-4-(3,4-dichlorobenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6-cyclopenteno-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6-cyclohepteno-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-ethyl-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-chloro-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5-chloro-6-methyl-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-nitro-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6-dimethyl-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-trifluoromethyl-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-methyl-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5-methyl-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6,7,8-tetrahydro-4-(3-nitrobenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6-cyclopenteno-4-(3-nitrobenzylamino)thieno[2,3-d]-pyrimidine;
2-(pyrazol-1-yl)-5,6-cyclohepteno-4-(3-nitrobenzylamino)thieno[2,3-d]-pyrimidine;
2-(pyrazol-1-yl)-6-ethyl-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-chloro-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5-chloro-6-methyl-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-nitro-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6-dimethyl-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-trifluoromethyl-4-(3-nitrobenzylamino)thieno[2,3-d]-pyrimidine;
2-(pyrazol-1-yl)-6-methyl-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5-methyl-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6,7,8-tetrahydro-4-(3,4-methylenedioxyphenethylamino)-[1]-benzylthieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6-cyclopenteno-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6-cyclohepteno-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-ethyl-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-chloro-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5-chloro-6-methyl-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-nitro-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6-dimethyl-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-trifluoromethyl-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-methyl-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5-methyl-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6,7,8-tetrahydro-4-(3,4-ethylenedioxybenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6-cyclopenteno-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6-cyclohepteno-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-ethyl-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-chloro-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5-chloro-6-methyl-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-nitro-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-5,6-dimethyl-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(pyrazol-1-yl)-6-trifluoromethyl-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine.

Analogous reaction of 1,2,4-triazole with the 4-arylalkylamino-substituted 2-chlorothieno[2,3-d]pyrimidine derivatives obtained under Example 1 gives the following compounds

2-(1,2,4-triazol-1-yl)-5-methyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6,7,8-tetrahydro-4-(3,4-methylenedioxybenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6-cyclopenteno-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6-cyclohepteno-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-ethyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-chloro-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5-chloro-6-methyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-nitro-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6-dimethyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-trifluoromethyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-methyl-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5-methyl-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6,7,8-tetrahydro-4-(3-chloro-4-methoxybenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6-cyclopenteno-4-(3-chloro-4-methyoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6-cyclohepteno-4-(3-chloro-4-methyoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-ethyl-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-chloro-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5-chloro-6-methyl-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-nitro-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6-dimethyl-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-trifluoromethyl-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-methyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5-methyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6,7,8-tetrahydro-4-(3,4-dimethoxybenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6-cyclopenteno-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6-cyclohepteno-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-ethyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-chloro-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5-chloro-6-methyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-nitro-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6-dimethyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-trifluoromethyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-methyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5-methyl-4-benzylaminothieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6,7,8-tetrahydro-4-benzylamino-[1]-benzylthieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6-cyclopenteno-4-benzylaminothieno[2,3-d]-pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6-cyclohepteno-4-benzylaminothieno[2,3-d]-pyrimidine;
2-(1,2,4-triazol-1-yl)-6-ethyl-4-benzylaminothieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-chloro-4-benzylaminothieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5-chloro-6-methyl-4-benzylaminothieno[2,3-d]-pyrimidine;
2-(1,2,4-triazol-1-yl)-6-nitro-4-benzylaminothieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6-dimethyl-4-benzylaminothieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-trifluoromethyl-4-benzylaminothieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-methyl-4-(4-fluorobenzylamino)thieno[2,3-d]-pyrimidine;
2-(1,2,4-triazol-1-yl)-5-methyl-4-(4-fluorobenzylamino)thieno[2,3-d]-pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6,7,8-tetrahydro-4-(4-fluorobenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6-cyclopenteno-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6-cyclohepteno-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-ethyl-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-chloro-4-(4-fluorobenzylamino)thieno[2,3-d]-pyrimidine;
2-(1,2,4-triazol-1-yl)-5-chloro-6-methyl-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-nitro-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6-dimethyl-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-trifluoromethyl-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-methyl-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5-methyl-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6,7,8-tetrahydro-4-(3,4-dichlorobenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6-cyclopenteno-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6-cyclohepteno-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-ethyl-4-(3,4-dichlorobenzylamino)thieno[2,3-d]-pyrimidine;
2-(1,2,4-triazol-1-yl)-6-chloro-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5-chloro-6-methyl-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-nitro-4-(3,4-dichlorobenzylamino)thieno[2,3-d]-pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6-dimethyl-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-trifluoromethyl-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-methyl-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5-methyl-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6,7,8-tetrahydro-4-(3-nitrobenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6-cyclopenteno-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6-cyclohepteno-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-ethyl-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-chloro-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5-chloro-6-methyl-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-nitro-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6-dimethyl-4-(3-nitrobenzylamino)thieno[2,3-d]-pyrimidine;
2-(1,2,4-triazol-1-yl)-6-trifluoromethyl-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-methyl-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5-methyl-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6,7,8-tetrahydro-4-(3,4-methylenedioxyphenethylamino)-[1]-benzylthieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6-cyclopenteno-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6-cyclohepteno-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-ethyl-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-chloro-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5-chloro-6-methyl-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-nitro-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6-dimethyl-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-trifluoromethyl-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-methyl-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5-methyl-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6,7,8-tetrahydro-4-(3,4-ethylenedioxybenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6-cyclopenteno-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6-cyclohepteno-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-ethyl-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-chloro-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5-chloro-6-methyl-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-nitro-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6-dimethyl-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-6-trifluoromethyl-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine.

Analogous reaction of 2-methylimidazole with the 4-arylalkylamino-substituted 2-chlorothieno[2,3-d]pyrimidine derivatives obtained under Example 1 gives the following compounds

2-(2-methylimidazol-1-yl)-5-methyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6,7,8-tetrahydro-4-(3,4-methylenedioxybenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine, amorph;
2-(2-methylimidazol-1-yl)-5,6-cyclopenteno-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6-cyclohepteno-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-ethyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-chloro-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5-chloro-6-methyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-nitro-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6-dimethyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-trifluoromethyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-methyl-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5-methyl-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6,7,8-tetrahydro-4-(3-chloro-4-methoxybenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6-cyclopenteno-4-(3-chloro-4-methyoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(1,2,4-triazol-1-yl)-5,6-cyclohepteno-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-ethyl-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-chloro-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5-chloro-6-methyl-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methyl-1-yl)-6-nitro-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6-dimethyl-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-trifluoromethyl-4-(3-chloro-4-methoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-methyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5-methyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6,7,8-tetrahydro-4-(3,4-dimethoxybenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6-cyclopenteno-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6-cyclohepteno-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-ethyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-chloro-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5-chloro-6-methyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-nitro-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6-dimethyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-trifluoromethyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-methyl-4-(3,4-dimethoxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5-methyl-4-benzylaminothieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6,7,8-tetrahydro-4-benzylamino-[1]-benzylthieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6-cyclopenteno-4-benzylaminothieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6-cyclohepteno-4-benzylaminothieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-ethyl-4-benzylaminothieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-chloro-4-benzylaminothieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5-chloro-6-methyl-4-benzylaminothieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-nitro-4-benzylaminothieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6-dimethyl-4-benzylaminothieno[2,3-d]-pyrimidine;
2-(2-methylimidazol-1-yl)-6-trifluoromethyl-4-benzylaminothieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-methyl-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5-methyl-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6,7,8-tetrahydro-4-(4-fluorobenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6-cyclopenteno-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6-cyclohepteno-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-ethyl-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-chloro-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5-chloro-6-methyl-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-nitro-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6-dimethyl-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-trifluoromethyl-4-(4-fluorobenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-methyl-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5-methyl-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6,7,8-tetrahydro-4-(3,4-dichlorobenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6-cyclopenteno-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6-cyclohepteno-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-ethyl-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-chloro-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5-chloro-6-methyl-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-nitro-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6-dimethyl-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-trifluoromethyl-4-(3,4-dichlorobenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-methyl-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5-methyl-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6,7,8-tetrahydro-4-(3-nitrobenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6-cyclopenteno-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6-cyclohepteno-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-ethyl-4-(3-nitrobenzylamino)thieno[2,3-d]-pyrimidine;
2-(2-methylimidazol-1-yl)-6-chloro-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5-chloro-6-methyl-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-nitro-4-(3-nitrobenzylamino)thieno[2,3-d]-pyrimidine;
2-(2-methylimidazol-1-yl)-5,6-dimethyl-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-trifluoromethyl-4-(3-nitrobenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-methyl-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5-methyl-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6,7,8-tetrahydro-4-(3,4-methylenedioxyphenethylamino)-[1]-benzylthieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6-cyclopenteno-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6-cyclohepteno-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-ethyl-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-chloro-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5-chloro-6-methyl-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-nitro-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6-dimethyl-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-trifluoromethyl-4-(3,4-methylenedioxyphenethylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-methyl-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5-methyl-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6,7,8-tetrahydro-4-(3,4-ethylenedioxybenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6-cyclopenteno-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6-cyclohepteno-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-ethyl-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-chloro-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5-chloro-6-methyl-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-nitro-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-5,6-dimethyl-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine;
2-(2-methylimidazol-1-yl)-6-trifluoromethyl-4-(3,4-ethylenedioxybenzylamino)thieno[2,3-d]pyrimidine.

EXAMPLE 3

5 g of 2-amino-5-methyl-3-ethoxycarbonylthiophene is dissolved in 40 ml of dioxane with 2.7 g of 3-cyanopyridine. Gaseous HCl is subsequently passed through the solution for 5 hours. Conventional work-up gives 6 g of 3,4-dihydro-4-oxo-2-(pyridin-3-yl)-6-methylthieno[2,3-d]pyrimidine. Replacement of the keto group with Cl with formation of the aromatic pyrimidine ring is carried out under standard conditions.

A mixture of 18 ml of POCl₃with 6 g of 3,4-dihydro-4-oxo-2-(pyridin-3-yl)-6-methylthieno[2,3-d]pyrimidine with addition of 1.8 ml of N,N-dimethylaniline is boiled for 4 hours. Conventional work-up gives 5 g of 4-chloro-2-(pyridin-3-yl)-6-methylthieno[2,3-d]pyrimidine.

Analogous Reaction of 3-cyanopyridine and Subsequent Reaction with POCl₃

of 2-amino-4-methyl-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyridin-3-yl)-5-methylthieno[2,3-d]pyrimidine;

of 2-amino-4,5,6,7-tetrahydro-3-ethoxycarbonylbenzothiophene gives 4-chloro-2-(pyridin-3-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine, m.p. 143°;

of 2-amino-4,5-cyclopenteno-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyridin-3-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine;

of 2-amino-4,5-cyclohepteno-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyridin-3-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine;

of 2-amino-5-ethyl-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyridin-3-yl)-6-ethylthieno[2,3-d]pyrimidine;

of 2-amino-5-chloro-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyridin-3-yl)-6-chlorothieno[2,3-d]pyrimidine;

of 2-amino-4-chloro-5-methyl-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyridin-3-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine;

of 2-amino-5-nitro-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyridin-3-yl)-6-nitrothieno[2,3-d]pyrimidine;

of 2-amino-4,5-dimethyl-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyridin-3-yl)-5,6-dimethylthieno[2,3-d]pyrimidine;

of 2-amino-5-trifluoromethyl-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyridin-3-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine.

Analogous Reaction of 5-cyanoisoxazole and Subsequent Reaction with POCl₃

of 2-amino-5-methyl-3-ethoxycarbonylthiophene gives 4-chloro-2-(isoxazol-5-yl)-6-methylthieno[2,3-d]pyrimidine;

of 2-amino-4-methyl-3-ethoxycarbonylthiophene gives 4-chloro-2-(isoxazol-5-yl)-5-methylthieno[2,3-d]pyrimidine;

of 2-amino-4,5,6,7-tetrahydro-3-ethoxycarbonylbenzothiophene gives 4-chloro-2-(isoxazol-5-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]-pyrimidine;

of 2-amino-4,5-cyclopenteno-3-ethoxycarbonylthiophene gives 4-chloro-2-(isoxazol-5-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine;

of 2-amino-4,5-cyclohepteno-3-ethoxycarbonylthiophene gives 4-chloro-2-(isoxazol-5-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine;

of 2-amino-5-ethyl-3-ethoxycarbonylthiophene gives 4-chloro-2-(isoxazol-5-yl)-6-ethylthieno[2,3-d]pyrimidine;

of 2-amino-5-chloro-3-ethoxycarbonylthiophene gives 4-chloro-2-(isoxazol-5-yl)-6-chlorothieno[2,3-d]pyrimidine;

of 2-amino-4-chloro-5-methyl-3-ethoxycarbonylthiophene gives 4-chloro-2-(isoxazol-5-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine;

of 2-amino-5-nitro-3-ethoxycarbonylthiophene gives 4-chloro-2-(isoxazol-5-yl)-6-nitrothieno[2,3-d]pyrimidine;

of 2-amino-4,5-dimethyl-3-ethoxycarbonylthiophene gives 4-chloro-2-(isoxazol-5-yl)-5,6-dimethylthieno[2,3-d]pyrimidine;

of 2-amino-5-trifluoromethyl-3-ethoxycarbonylthiophene gives 4-chloro-2-(isoxazol-5-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine.

Analogous Reaction of 2-cyanopyrazine and Subsequent Reaction with POCl₃

of 2-amino-5-methyl-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyrazin-2-yl)-6-methylthieno[2,3-d]pyrimidine;

of 2-amino-4-methyl-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyrazin-2-yl)-5-methylthieno[2,3-d]pyrimidine;

of 2-amino-4,5,6,7-tetrahydro-3-ethoxycarbonylbenzothiophene gives 4-chloro-2-(pyrazin-2-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]-pyrimidine;

of 2-amino-4,5-cyclopenteno-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyrazin-2-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine;

of 2-amino-4,5-cyclohepteno-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyrazin-2-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine;

of 2-amino-5-ethyl-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyrazin-2-yl)-6-ethylthieno[2,3-d]pyrimidine;

of 2-amino-5-chloro-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyrazin-2-yl)-6-chlorothieno[2,3-d]pyrimidine;

of 2-amino-4-chloro-5-methyl-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyrazin-2-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine;

of 2-amino-5-nitro-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyrazin-2-yl)-6-nitrothieno[2,3-d]pyrimidine;

of 2-amino-4,5-dimethyl-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyrazin-2-yl)-5,6-dimethylthieno[2,3-d]pyrimidine;

of 2-amino-5-trifluoromethyl-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyrazin-2-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine.

Analogous Reaction of 2-cyanopyridine and Subsequent Reaction with POCl₃

of 2-amino-5-methyl-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyridin-2-yl)-6-methylthieno[2,3-d]pyrimidine;

of 2-amino-4-methyl-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyridin-2-yl)-5-methylthieno[2,3-d]pyrimidine;

of 2-amino-4,5,6,7-tetrahydro-3-ethoxycarbonylbenzothiophene gives 4-chloro-2-(pyridin-2-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

of 2-amino-4,5-cyclopenteno-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyridin-2-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine;

of 2-amino-4,5-cyclohepteno-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyridin-2-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine;

of 2-amino-5-ethyl-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyridin-2-yl)-6-ethylthieno[2,3-d]pyrimidine;

of 2-amino-5-chloro-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyridin-2-yl)-6-chlorothieno[2,3-d]pyrimidine;

of 2-amino-4-chloro-5-methyl-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyridin-2-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine;

of 2-amino-5-nitro-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyridin-2-yl)-6-nitrothieno[2,3-d]pyrimidine;

of 2-amino-4,5-dimethyl-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyridin-2-yl)-5,6-dimethylthieno[2,3-d]pyrimidine;

of 2-amino-5-trifluoromethyl-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyridin-2-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine.

Analogous Reaction of 4-cyanopyridine and Subsequent Reaction with POCl₃

of 2-amino-5-methyl-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyridin-4-yl)-6-methylthieno[2,3-d]pyrimidine;

of 2-amino-4-methyl-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyridin-4-yl)-5-methylthieno[2,3-d]pyrimidine;

of 2-amino-4,5,6,7-tetrahydro-3-ethoxycarbonylbenzothiophene gives 4-chloro-2-(pyridin-4-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

of 2-amino-4,5-cyclopenteno-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyridin-4-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine;

of 2-amino-4,5-cyclohepteno-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyridin-4-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine;

of 2-amino-5-ethyl-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyridin-4-yl)-6-ethylthieno[2,3-d]pyrimidine;

of 2-amino-5-chloro-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyridin-4-yl)-6-chlorothieno[2,3-d]pyrimidine;

of 2-amino-4-chloro-5-methyl-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyridin-4-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine;

of 2-amino-5-nitro-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyridin-4-yl)-6-nitrothieno[2,3-d]pyrimidine;

of 2-amino-4,5-dimethyl-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyridin-4-yl)-5,6-dimethylthieno[2,3-d]pyrimidine;

of 2-amino-5-trifluoromethyl-3-ethoxycarbonylthiophene gives 4-chloro-2-(pyridin-4-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine.

EXAMPLE 4

Analogously to Example 1, reaction of 3,4-methylenedioxybenzylamine

with 4-chloro-2-(pyridin-3-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-methylenedioxybenzylamino)-6-methylthieno-[2,3-d]pyrimidine;
with 4-chloro-2-(pyridin-3-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-methylenedioxybenzylamino)-5-methylthieno-[2,3-d]pyrimidine;
with 4-chloro-2-(pyridin-3-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-methylenedioxybenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine, m.p. 215°;
with 4-chloro-2-(pyridin-3-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-methylenedioxybenzylamino)-5,6-cyclopentenothieno[2,3-d]pyrimidine;
with 4-chloro-2-(pyridin-3-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-methylenedioxybenzylamino)-5,6-cyclohepteno thieno[2,3-d]pyrimidine;
with 4-chloro-2-(pyridin-3-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-methylenedioxybenzylamino)-6-ethylthieno-[2,3-d]pyrimidine;
with 4-chloro-2-(pyridin-3-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-methylenedioxybenzylamino)-6-chlorothieno-[2,3-d]pyrimidine;
with 4-chloro-2-(pyridin-3-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-methylenedioxybenzylamino)-5-chloro-6-methylthieno[2,3-d]pyrimidine;
with 4-chloro-2-(pyridin-3-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-methylenedioxybenzylamino)-6-nitrothieno-[2,3-d]pyrimidine;
with 4-chloro-2-(pyridin-3-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-methylenedioxybenzylamino)-5,6-dimethylthieno[2,3-d]pyrimidine;
with 4-chloro-2-(pyridin-3-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-methylenedioxybenzylamino)-6-trifluoromethylthieno[2,3-d]pyrimidine;
with 4-chloro-2-(isoxazol-5-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-methylenedioxybenzylamino)-6-methylthieno-[2,3-d]pyrimidine;
with 4-chloro-2-(isoxazol-5-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-methylenedioxybenzylamino)-5-methylthieno-[2,3-d]pyrimidine;
with 4-chloro-2-(isoxazol-5-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]-pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-methylenedioxybenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;
with 4-chloro-2-(isoxazol-5-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives
2-(isoxazol-5-yl)-4-(3,4-methylenedioxybenzylamino)-5,6-cyclopentenothieno[2,3-d]pyrimidine;
with 4-chloro-2-(isoxazol-5-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-methylenedioxybenzylamino)-5,6-cycloheptenothieno[2,3-d]pyrimidine;
with 4-chloro-2-(isoxazol-5-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-methylenedioxybenzylamino)-6-ethylthieno-[2,3-d]pyrimidine;
with 4-chloro-2-(isoxazol-5-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-methylenedioxybenzylamino)-6-chlorothieno-[2,3-d]pyrimidine;
with 4-chloro-2-(isoxazol-5-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-methylenedioxybenzylamino)-5-chloro-6-methylthieno[2,3-d]pyrimidine;
with 4-chloro-2-(isoxazol-5-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-methylenedioxybenzylamino)-6-nitrothieno-[2,3-d]pyrimidine;
with 4-chloro-2-(isoxazol-5-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-methylenedioxybenzylamino)-5,6-dimethylthieno[2,3-d]pyrimidine;
with 4-chloro-2-(isoxazol-5-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-methylenedioxybenzylamino)-6-trifluoromethylthieno[2,3-d]pyrimidine;
with 4-chloro-2-(pyrazin-2-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-methylenedioxybenzylamino)-6-methylthieno-[2,3-d]pyrimidine;
with 4-chloro-2-(pyrazin-2-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-methylenedioxybenzylamino)-5-methylthieno-[2,3-d]pyrimidine;
with 4-chloro-2-(pyrazin-2-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-methylenedioxybenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;
with 4-chloro-2-(pyrazin-2-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-methylenedioxybenzylamino)-5,6-cyclopentenothieno[2,3-d]pyrimidine;
with 4-chloro-2-(pyrazin-2-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-methylenedioxybenzylamino)-5,6-cycloheptenothieno[2,3-d]pyrimidine;
with 4-chloro-2-(pyrazin-2-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-methylenedioxybenzylamino)-6-ethylthieno-[2,3-d]pyrimidine;
with 4-chloro-2-(pyrazin-2-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-methylenedioxybenzylamino)-6-chlorothieno-[2,3-d]pyrimidine;
with 4-chloro-2-(pyrazin-2-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-methylenedioxybenzylamino)-5-chloro-6-methylthieno[2,3-d]pyrimidine;
with 4-chloro-2-(pyrazin-2-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-methylenedioxybenzylamino)-6-nitrothieno-[2,3-d]pyrimidine;
with 4-chloro-2-(pyrazin-2-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-methylenedioxybenzylamino)-5,6-dimethylthieno[2,3-d]pyrimidine;
with 4-chloro-2-(pyrazin-2-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-methylenedioxybenzylamino)-6-trifluoromethylthieno[2,3-d]pyrimidine.
with 4-chloro-2-(pyridin-2-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-methylenedioxybenzylamino)-6-methylthieno-[2,3-d]pyrimidine;
with 4-chloro-2-(pyridin-2-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-methylenedioxybenzylamino)-5-methylthieno-[2,3-d]pyrimidine;
with 4-chloro-2-(pyridin-2-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-methylenedioxybenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;
with 4-chloro-2-(pyridin-2-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-methylenedioxybenzylamino)-5,6-cyclopentenothieno[2,3-d]pyrimidine;
with 4-chloro-2-(pyridin-2-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-methylenedioxybenzylamino)-5,6-cycloheptenothieno[2,3-d]pyrimidine;
with 4-chloro-2-(pyridin-2-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-methylenedioxybenzylamino)-6-ethylthieno-[2,3-d]pyrimidine;
with 4-chloro-2-(pyridin-2-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-methylenedioxybenzylamino)-6-chlorothieno-[2,3-d]pyrimidine;
with 4-chloro-2-(pyridin-2-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-methylenedioxybenzylamino)-5-chloro-6-methylthieno[2,3-d]pyrimidine;
with 4-chloro-2-(pyridin-2-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-methylenedioxybenzylamino)-6-nitrothieno-[2,3-d]pyrimidine;
with 4-chloro-2-(pyridin-2-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-methylenedioxybenzylamino)-5,6-dimethylthieno[2,3-d]pyrimidine;
with 4-chloro-2-(pyridin-2-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-methylenedioxybenzylamino)-6-trifluoromethylthieno[2,3-d]pyrimidine;
with 4-chloro-2-(pyridin-4-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-methylenedioxybenzylamino)-6-methylthieno-[2,3-d]pyrimidine;
with 4-chloro-2-(pyridin-4-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-methylenedioxybenzylamino)-5-methylthieno-[2,3-d]pyrimidine;
with 4-chloro-2-(pyridin-4-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-methylenedioxybenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine, m.p. 185°;
with 4-chloro-2-(pyridin-4-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-methylenedioxybenzylamino)-5,6-cyclopentenothieno[2,3-d]pyrimidine;
with 4-chloro-2-(pyridin-4-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-methylenedioxybenzylamino)-5,6-cycloheptenothieno[2,3-d]pyrimidine;
with 4-chloro-2-(pyridin-4-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-methylenedioxybenzylamino)-6-ethylthieno-[2,3-d]pyrimidine;
with 4-chloro-2-(pyridin-4-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-methylenedioxybenzylamino)-6-chlorothieno-[2,3-d]pyrimidine;
with 4-chloro-2-(pyridin-4-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-methylenedioxybenzylamino)-5-chloro-6-methylthieno[2,3-d]pyrimidine;
with 4-chloro-2-(pyridin-4-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-methylenedioxybenzylamino)-6-nitrothieno-[2,3-d]pyrimidine;
with 4-chloro-2-(pyridin-4-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-methylenedioxybenzylamino)-5,6-dimethylthieno[2,3-d]pyrimidine;
with 4-chloro-2-(pyridin-4-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-methylenedioxybenzylamino)-6-trifluoromethylthieno[2,3-d]pyrimidine.

Analogous Reaction of 3-chloro-4-methoxybenzylamine

with 4-chloro-2-(pyridin-3-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3-chloro-4-methoxybenzylamino)-6-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3-chloro-4-methoxybenzylamino)-5-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3-chloro-4-methoxybenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3-chloro-4-methoxybenzylamino)-5,6-cyclopentenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3-chloro-4-methoxybenzylamino)-5,6-cycloheptenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3-chloro-4-methoxybenzylamino)-6-ethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3-chloro-4-methoxybenzylamino)-6-chlorothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3-chloro-4-methoxybenzylamino)-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3-chloro-4-methoxybenzylamino)-6-nitrothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3-chloro-4-methoxybenzylamino)-5,6-dimethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3-chloro-4-methoxybenzylamino)-6-trifluoromethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3-chloro-4-methoxybenzylamino)-6-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3-chloro-4-methoxybenzylamino)-5-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]-pyrimidine gives 2-(isoxazol-5-yl)-4-(3-chloro-4-methoxybenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3-chloro-4-methoxybenzylamino)-5,6-cyclopentenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3-chloro-4-methoxybenzylamino)-5,6-cycloheptenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3-chloro-4-methoxybenzylamino)-6-ethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3-chloro-4-methoxybenzylamino)-6-chlorothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3-chloro-4-methoxybenzylamino)-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3-chloro-4-methoxybenzylamino)-6-nitrothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3-chloro-4-methoxybenzylamino)-5,6-dimethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3-chloro-4-methoxybenzylamino)-6-trifluoromethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3-chloro-4-methoxybenzylamino)-6-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3-chloro-4-methoxybenzylamino)-5-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3-chloro-4-methoxybenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3-chloro-4-methoxybenzylamino)-5,6-cyclopentenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3-chloro-4-methoxybenzylamino)-5,6-cycloheptenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3-chloro-4-methoxybenzylamino)-6-ethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3-chloro-4-methoxybenzylamino)-6-chlorothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3-chloro-4-methoxybenzylamino)-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3-chloro-4-methoxybenzylamino)-6-nitrothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3-chloro-4-methoxybenzylamino)-5,6-dimethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3-chloro-4-methoxybenzylamino)-6-trifluoromethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3-chloro-4-methoxybenzylamino)-6-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3-chloro-4-methoxybenzylamino)-5-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3-chloro-4-methoxybenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3-chloro-4-methoxybenzylamino)-5,6-cyclopentenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3-chloro-4-methoxybenzylamino)-5,6-cycloheptenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3-chloro-4-methoxybenzylamino)-6-ethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3-chloro-4-methoxybenzylamino)-6-chlorothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3-chloro-4-methoxybenzylamino)-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3-chloro-4-methoxybenzylamino)-6-nitrothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3-chloro-4-methoxybenzylamino)-5,6-dimethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3-chloro-4-methoxybenzylamino)-6-trifluoromethylthieno[2,3-d]pyrimidine.

with 4-chloro-2-(pyridin-4-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3-chloro-4-methoxybenzylamino)-6-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3-chloro-4-methoxybenzylamino)-5-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3-chloro-4-methoxybenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3-chloro-4-methoxybenzylamino)-5,6-cyclopentenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3-chloro-4-methoxybenzylamino)-5,6-cycloheptenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3-chloro-4-methoxybenzylamino)-6-ethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3-chloro-4-methoxybenzylamino)-6-chlorothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3-chloro-4-methoxybenzylamino)-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3-chloro-4-methoxybenzylamino)-6-nitrothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3-chloro-4-methoxybenzylamino)-5,6-dimethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3-chloro-4-methoxybenzylamino)-6-trifluoromethylthieno[2,3-d]pyrimidine.

Analogous Reaction of 3,4-dimethoxybenzylamine

with 4-chloro-2-(pyridin-3-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-dimethoxybenzylamino)-6-methylthieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-dimethoxybenzylamino)-5-methylthieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6,7,8-tetrahydro-[f]-benzylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-dimethoxybenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-dimethoxybenzylamino)-5,6-cyclopentenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-dimethoxybenzylamino)-5,6-cycloheptenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-dimethoxybenzylamino)-6-ethylthieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-dimethoxybenzylamino)-6-chlorothieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-dimethoxybenzylamino)-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-dimethoxybenzylamino)-6-nitrothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-dimethoxybenzylamino)-5,6-dimethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-dimethoxybenzylamino)-6-trifluoromethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-dimethoxybenzylamino)-6-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-dimethoxybenzylamino)-5-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]-pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-dimethoxybenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-dimethoxybenzylamino)-5,6-cyclopentenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-dimethoxybenzylamino)-5,6-cycloheptenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-dimethoxybenzylamino)-6-ethylthieno[2,3-d]-pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-dimethoxybenzylamino)-6-chlorothieno[2,3-d]-pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-dimethoxybenzylamino)-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-dimethoxybenzylamino)-6-nitrothieno[2,3-d]-pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-dimethoxybenzylamino)-5,6-dimethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-dimethoxybenzylamino)-6-trifluoromethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-dimethoxybenzylamino)-6-methylthieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-dimethoxybenzylamino)-5-methylthieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-dimethoxybenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-dimethoxybenzylamino)-5,6-cyclopentenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-dimethoxybenzylamino)-5,6-cycloheptenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-dimethoxybenzylamino)-6-ethylthieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-dimethoxybenzylamino)-6-chlorothieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-dimethoxybenzylamino)-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-dimethoxybenzylamino)-6-nitrothieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-dimethoxybenzylamino)-5,6-dimethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-dimethoxybenzylamino)-6-trifluoromethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-dimethoxybenzylamino)-6-methylthieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-dimethoxybenzylamino)-5-methylthieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-dimethoxybenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-dimethoxybenzylamino)-5,6-cyclopentenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-dimethoxybenzylamino)-5,6-cycloheptenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-dimethoxybenzylamino)-6-ethylthieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-dimethoxybenzylamino)-6-chlorothieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-dimethoxybenzylamino)-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-dimethoxybenzylamino)-6-nitrothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-dimethoxybenzylamino)-5,6-dimethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-dimethoxybenzylamino)-6-trifluoromethylthieno-[2,3-d]pyrimidine.

with 4-chloro-2-(pyridin-4-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-dimethoxybenzylamino)-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-dimethoxybenzylamino)-5-methylthieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-dimethoxybenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-dimethoxybenzylamino)-5,6-cyclopentenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-dimethoxybenzylamino)-5,6-cycloheptenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-dimethoxybenzylamino)-6-ethylthieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-dimethoxybenzylamino)-6-chlorothieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-dimethoxybenzylamino)-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-dimethoxybenzylamino)-6-nitrothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-dimethoxybenzylamino)-5,6-dimethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-dimethoxybenzylamino)-6-trifluoromethylthieno-[2,3-d]pyrimidine.

Analogous Reaction of benzylamine

with 4-chloro-2-(pyridin-3-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-benzylamino-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-benzylamino-5-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-benzylamino-5,6,7,8-tetrahydro-[1]-benzylthieno-[2,3-d]pyrimidine, m.p. 189°;

with 4-chloro-2-(pyridin-3-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-benzylamino-5,6-cyclopentenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-benzylamino-5,6-cycloheptenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-benzylamino-6-ethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-benzylamino-6-chlorothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-benzylamino-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-benzylamino-6-nitrothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-benzylamino-5,6-dimethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-benzylamino-6-trifluoromethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-benzylamino-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-benzylamino-5-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]-pyrimidine gives 2-(isoxazol-5-yl)-4-benzylamino-5,6,7,8-tetrahydro-[1]-benzylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-benzylamino-5,6-cyclopentenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-benzylamino-5,6-cycloheptenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-benzylamino-6-ethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-benzylamino-6-chlorothieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-benzylamino-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-benzylamino-6-nitrothieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-benzylamino-5,6-dimethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-benzylamino-6-trifluoromethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-benzylamino-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-benzylamino-5-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-benzylamino-5,6,7,8-tetrahydro-[1]-benzylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-benzylamino-5,6-cyclopentenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-benzylamino-5,6-cycloheptenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-benzylamino-6-ethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-benzylamino-6-chlorothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-benzylamino-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-benzylamino-6-nitrothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-benzylamino-5,6-dimethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-benzylamino-6-trifluoromethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-benzylamino-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-benzylamino-5-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-benzylamino-5,6,7,8-tetrahydro-[1]-benzylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-benzylamino-5,6-cyclopentenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-benzylamino-5,6-cycloheptenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-benzylamino-6-ethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-benzylamino-6-chlorothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-benzylamino-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-benzylamino-6-nitrothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-benzylamino-5,6-dimethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-benzylamino-6-trifluoromethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-benzylamino-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-benzylamino-5-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-benzylamino-5,6,7,8-tetrahydro-[1]-benzylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-benzylamino-5,6-cyclopentenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-benzylamino-5,6-cycloheptenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-benzylamino-6-ethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-benzylamino-6-chlorothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-benzylamino-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-benzylamino-6-nitrothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-benzylamino-5,6-dimethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-benzylamino-6-trifluoromethylthieno[2,3-d]pyrimidine.

Analogous Reaction of 4-fluorobenzylamine

with 4-chloro-2-(pyridin-3-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(4-fluorobenzylamino)-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(4-fluorobenzylamino)-5-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(4-fluorobenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(4-fluorobenzylamino)-5,6-cyclopentenothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(4-fluorobenzylamino)-5,6-cycloheptenothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(4-fluorobenzylamino)-6-ethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(4-fluorobenzylamino)-6-chlorothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(4-fluorobenzylamino)-5-chloro-6-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(4-fluorobenzylamino)-6-nitrothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(4-fluorobenzylamino)-5,6-dimethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(4-fluorobenzylamino)-6-trifluoromethylthieno[2,3-d]-pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(4-fluorobenzylamino)-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(4-fluorobenzylamino)-5-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]-pyrimidine gives 2-(isoxazol-5-yl)-4-(4-fluorobenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(4-fluorobenzylamino)-5,6-cyclopentenothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(4-fluorobenzylamino)-5,6-cycloheptenothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(4-fluorobenzylamino)-6-ethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(4-fluorobenzylamino)-6-chlorothieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(4-fluorobenzylamino)-5-chloro-6-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(4-fluorobenzylamino)-6-nitrothieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(4-fluorobenzylamino)-5,6-dimethylthieno[2,3-d]-pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(4-fluorobenzylamino)-6-trifluoromethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(4-fluorobenzylamino)-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(4-fluorobenzylamino)-5-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(4-fluorobenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(4-fluorobenzylamino)-5,6-cyclopentenothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(4-fluorobenzylamino)-5,6-cycloheptenothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(4-fluorobenzylamino)-6-ethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(4-fluorobenzylamino)-6-chlorothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(4-fluorobenzylamino)-5-chloro-6-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(4-fluorobenzylamino)-6-nitrothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(4-fluorobenzylamino)-5,6-dimethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(4-fluorobenzylamino)-6-trifluoromethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(4-fluorobenzylamino)-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(4-fluorobenzylamino)-5-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(4-fluorobenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(4-fluorobenzylamino)-5,6-cyclopentenothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(4-fluorobenzylamino)-5,6-cycloheptenothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(4-fluorobenzylamino)-6-ethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(4-fluorobenzylamino)-6-chlorothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(4-fluorobenzylamino)-5-chloro-6-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(4-fluorobenzylamino)-6-nitrothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(4-fluorobenzylamino)-5,6-dimethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(4-fluorobenzylamino)-6-trifluoromethylthieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(4-fluorobenzylamino)-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(4-fluorobenzylamino)-5-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(4-fluorobenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(4-fluorobenzylamino)-5,6-cyclopentenothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(4-fluorobenzylamino)-5,6-cycloheptenothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(4-fluorobenzylamino)-6-ethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(4-fluorobenzylamino)-6-chlorothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(4-fluorobenzylamino)-5-chloro-6-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(4-fluorobenzylamino)-6-nitrothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(4-fluorobenzylamino)-5,6-dimethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(4-fluorobenzylamino)-6-trifluoromethylthieno[2,3-d]-pyrimidine.

Analogous Reaction of 3,4-dichlorobenzylamine

with 4-chloro-2-(pyridin-3-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-dichlorobenzylamino)-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-dichlorobenzylamino)-5-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-dichlorobenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-dichlorobenzylamino)-5,6-cyclopentenothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-dichlorobenzylamino)-5,6-cycloheptenothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-dichlorobenzylamino)-6-ethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-dichlorobenzylamino)-6-chlorothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-dichlorobenzylamino)-5-chloro-6-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-dichlorobenzylamino)-6-nitrothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-dichlorobenzylamino)-5,6-dimethylthieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-dichlorobenzylamino)-6-trifluoromethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-dichlorobenzylamino)-6-methylthieno[2,3-d]-pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-dichlorobenzylamino)-5-methylthieno[2,3-d]-pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]-pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-dichlorobenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-dichlorobenzylamino)-5,6-cyclopentenothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-dichlorobenzylamino)-5,6-cycloheptenothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-dichlorobenzylamino)-6-ethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-dichlorobenzylamino)-6-chlorothieno[2,3-d]-pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-dichlorobenzylamino)-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-dichlorobenzylamino)-6-nitrothieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-dichlorobenzylamino)-5,6-dimethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-dichlorobenzylamino)-6-trifluoromethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-dichlorobenzylamino)-6-methylthieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-dichlorobenzylamino)-5-methylthieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-dichlorobenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-dichlorobenzylamino)-5,6-cyclopentenothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-dichlorobenzylamino)-5,6-cycloheptenothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-dichlorobenzylamino)-6-ethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-dichlorobenzylamino)-6-chlorothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-dichlorobenzylamino)-5-chloro-6-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-dichlorobenzylamino)-6-nitrothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-dichlorobenzylamino)-5,6-dimethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-dichlorobenzylamino)-6-trifluoromethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-dichlorobenzylamino)-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-dichlorobenzylamino)-5-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-dichlorobenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-dichlorobenzylamino)-5,6-cyclopentenothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-dichlorobenzylamino)-5,6-cycloheptenothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-dichlorobenzylamino)-6-ethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-dichlorobenzylamino)-6-chlorothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-dichlorobenzylamino)-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-dichlorobenzylamino)-6-nitrothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-dichlorobenzylamino)-5,6-dimethylthieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-dichlorobenzylamino)-6-trifluoromethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-dichlorobenzylamino)-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-dichlorobenzylamino)-5-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-dichlorobenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-dichlorobenzylamino)-5,6-cyclopentenothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-dichlorobenzylamino)-5,6-cycloheptenothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-dichlorobenzylamino)-6-ethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-dichlorobenzylamino)-6-chlorothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-dichlorobenzylamino)-5-chloro-6-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-dichlorobenzylamino)-6-nitrothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-dichlorobenzylamino)-5,6-dimethylthieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-dichlorobenzylamino)-6-trifluoromethylthieno-[2,3-d]pyrimidine.

Analogous Reaction of 3-nitrobenzylamine

with 4-chloro-2-(pyridin-3-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3-nitrobenzylamino)-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3-nitrobenzylamino)-5-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3-nitrobenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3-nitrobenzylamino)-5,6-cyclopentenothieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3-nitrobenzylamino)-5,6-cycloheptenothieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3-nitrobenzylamino)-6-ethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3-nitrobenzylamino)-6-chlorothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3-nitrobenzylamino)-5-chloro-6-methylthieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3-nitrobenzylamino)-6-nitrothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3-nitrobenzylamino)-5,6-dimethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3-nitrobenzylamino)-6-trifluoromethylthieno[2,3-d]-pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3-nitrobenzylamino)-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3-nitrobenzylamino)-5-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]-pyrimidine gives 2-(isoxazol-5-yl)-4-(3-nitrobenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3-nitrobenzylamino)-5,6-cyclopentenothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4(3-nitrobenzylamino)-5,6-cycloheptenothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3-nitrobenzylamino)-6-ethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3-nitrobenzylamino)-6-chlorothieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3-nitrobenzylamino)-5-chloro-6-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3-nitrobenzylamino)-6-nitrothieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3-nitrobenzylamino)-5,6-dimethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3-nitrobenzylamino)-6-trifluoromethylthieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3-nitrobenzylamino)-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3-nitrobenzylamino)-5-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3-nitrobenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3-nitrobenzylamino)-5,6-cyclopentenothieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3-nitrobenzylamino)-5,6-cycloheptenothieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3-nitrobenzylamino)-6-ethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3-nitrobenzylamino)-6-chlorothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3-nitrobenzylamino)-5-chloro-6-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3-nitrobenzylamino)-6-nitrothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3-nitrobenzylamino)-5,6-dimethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3-nitrobenzylamino)-6-trifluoromethylthieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3-nitrobenzylamino)-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3-nitrobenzylamino)-5-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3-nitrobenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3-nitrobenzylamino)-5,6-cyclopentenothieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3-nitrobenzylamino)-5,6-cycloheptenothieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3-nitrobenzylamino)-6-ethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3-nitrobenzylamino)-6-chlorothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3-nitrobenzylamino)-5-chloro-6-methylthieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3-nitrobenzylamino)-6-nitrothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3-nitrobenzylamino)-5,6-dimethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3-nitrobenzylamino)-6-trifluoromethylthieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3-nitrobenzylamino)-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3-nitrobenzylamino)-5-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3-nitrobenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3-nitrobenzylamino)-5,6-cyclopentenothieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3-nitrobenzylamino)-5,6-cycloheptenothieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3-nitrobenzylamino)-6-ethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3-nitrobenzylamino)-6-chlorothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3-nitrobenzylamino)-5-chloro-6-methylthieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3-nitrobenzylamino)-6-nitrothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3-nitrobenzylamino)-5,6-dimethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3-nitrobenzylamino)-6-trifluoromethylthieno[2,3-d]-pyrimidine.

Analogous Reaction of 3,4-methylenedioxyphenethylamine

with 4-chloro-2-(pyridin-3-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-methylenedioxyphenethylamino)-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-methylenedioxyphenethylamino)-5-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-methylenedioxyphenethylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-methylenedioxyphenethylamino)-5,6-cyclopentenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-methylenedioxyphenethylamino)-5,6-cycloheptenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-methylenedioxyphenethylamino)-6-ethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-methylenedioxyphenethylamino)-6-chloro-thieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-methylenedioxyphenethylamino)-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-methylenedioxyphenethylamino)-6-nitrothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-methylenedioxyphenethylamino)-5,6-dimethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-methylenedioxyphenethylamino)-6-trifluoromethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-methylenedioxyphenethylamino)-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-methylenedioxyphenethylamino)-5-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]-pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-methylenedioxyphenethylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-methylenedioxyphenethylamino)-5,6-cyclopentenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-methylenedioxyphenethylamino)-5,6-cycloheptenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-methylenedioxyphenethylamino)-6-ethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-methylenedioxyphenethylamino)-6-chlorothieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-methylenedioxyphenethylamino)-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-methylenedioxyphenethylamino)-6-nitrothieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-methylenedioxyphenethylamino)-5,6-dimethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-methylenedioxyphenethylamino)-6-trifluoromethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-methylenedioxyphenethylamino)-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-methylenedioxyphenethylamino)-5-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-methylenedioxyphenethylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-methylenedioxyphenethylamino)-5,6-cyclopentenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-methylenedioxyphenethylamino)-5,6-cycloheptenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-methylenedioxyphenethylamino)-6-ethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-methylenedioxyphenethylamino)-6-chlorothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-methylenedioxyphenethylamino)-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-methylenedioxyphenethylamino)-6-nitrothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-methylenedioxyphenethylamino)-5,6-dimethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-methylenedioxyphenethylamino)-6-trifluoromethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-methylenedioxyphenethylamino)-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-methylenedioxyphenethylamino)-5-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-methylenedioxyphenethylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-methylenedioxyphenethylamino)-5,6-cyclopentenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-methylenedioxyphenethylamino)-5,6-cycloheptenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-methylenedioxyphenethylamino)-6-ethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-methylenedioxyphenethylamino)-6-chlorothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-methylenedioxyphenethylamino)-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-methylenedioxyphenethylamino)-6-nitrothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-methylenedioxyphenethylamino)-5,6-dimethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-methylenedioxyphenethylamino)-6-trifluoromethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-methylenedioxyphenethylamino)-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-methylenedioxyphenethylamino)-5-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-methylenedioxyphenethylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-methylenedioxyphenethylamino)-5,6-cyclopentenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-methylenedioxyphenethylamino)-5,6-cycloheptenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-methylenedioxyphenethylamino)-6-ethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-methylenedioxyphenethylamino)-6-chlorothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-methylenedioxyphenethylamino)-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-methylenedioxyphenethylamino)-6-nitrothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-methylenedioxyphenethylamino)-5,6-dimethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-methylenedioxyphenethylamino)-6-trifluoromethylthieno[2,3-d]pyrimidine.

Analogous Reaction of 3,4-ethylenedioxybenzylamine

with 4-chloro-2-(pyridin-3-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-ethylenedioxybenzylamino)-6-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-ethylenedioxybenzylamino)-5-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-ethylenedioxybenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-ethylenedioxybenzylamino)-5,6-cyclopentenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-ethylenedioxybenzylamino)-5,6-cycloheptenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-ethylenedioxybenzylamino)-6-ethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-ethylenedioxybenzylamino)-6-chlorothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-ethylenedioxybenzylamino)-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-ethylenedioxybenzylamino)-6-nitrothieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-ethylenedioxybenzylamino)-5,6-dimethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-(3,4-ethylenedioxybenzylamino)-6-trifluoromethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-ethylenedioxybenzylamino)-6-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-ethylenedioxybenzylamino)-5-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]-pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-ethylenedioxybenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-ethylenedioxybenzylamino)-5,6-cyclopentenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-ethylenedioxybenzylamino)-5,6-cycloheptenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-ethylenedioxybenzylamino)-6-ethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-ethylenedioxybenzylamino)-6-chlorothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-ethylenedioxybenzylamino)-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-ethylenedioxybenzylamino)-6-nitrothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-ethylenedioxybenzylamino)-5,6-dimethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-(3,4-ethylenedioxybenzylamino)-6-trifluoromethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-ethylenedioxybenzylamino)-6-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-ethylenedioxybenzylamino)-5-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-ethylenedioxybenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-ethylenedioxybenzylamino)-5,6-cyclopentenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-ethylenedioxybenzylamino)-5,6-cycloheptenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-ethylenedioxybenzylamino)-6-ethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-ethylenedioxybenzylamino)-6-chlorothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-ethylenedioxybenzylamino)-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-ethylenedioxybenzylamino)-6-nitrothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-ethylenedioxybenzylamino)-5,6-dimethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-(3,4-ethylenedioxybenzylamino)-6-trifluoromethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-ethylenedioxybenzylamino)-6-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-ethylenedioxybenzylamino)-5-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-ethylenedioxybenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-ethylenedioxybenzylamino)-5,6-cyclopentenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-ethylenedioxybenzylamino)-5,6-cycloheptenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-ethylenedioxybenzylamino)-6-ethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-ethylenedioxybenzylamino)-6-chlorothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-ethylenedioxybenzylamino)-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-ethylenedioxybenzylamino)-6-nitrothieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-ethylenedioxybenzylamino)-5,6-dimethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-(3,4-ethylenedioxybenzylamino)-6-trifluoromethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-ethylenedioxybenzylamino)-6-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-ethylenedioxybenzylamino)-5-methylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-ethylenedioxybenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-ethylenedioxybenzylamino)-5,6-cyclopentenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-ethylenedioxybenzylamino)-5,6-cycloheptenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-ethylenedioxybenzylamino)-6-ethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-ethylenedioxybenzylamino)-6-chlorothieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-ethylenedioxybenzylamino)-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-ethylenedioxybenzylamino)-6-nitrothieno[2,3-d]-pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-ethylenedioxybenzylamino)-5,6-dimethylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-(3,4-ethylenedioxybenzylamino)-6-trifluoromethylthieno[2,3-d]pyrimidine.

Analogous Reaction of phenethylamine

with 4-chloro-2-(pyridin-3-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-phenethylamino-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-phenethylamino-5-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-phenethylamino-5,6,7,8-tetrahydro-[1]-benzylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-phenethylamino-5,6-cyclopentenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-phenethylamino-5,6-cycloheptenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-phenethylamino-6-ethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-phenethylamino-6-chlorothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-phenethylamino-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-phenethylamino-6-nitrothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-phenethylamino-5,6-dimethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-3-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyridin-3-yl)-4-phenethylamino-6-trifluoromethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-phenethylamino-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-phenethylamino-5-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]-pyrimidine gives 2-(isoxazol-5-yl)-4-phenethylamino-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-phenethylamino-5,6-cyclopentenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-phenethylamino-5,6-cycloheptenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-phenethylamino-6-ethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-phenethylamino-6-chlorothieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-phenethylamino-5-chloro-6-methylthieno[2,3-d]-pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-phenethylamino-6-nitrothieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-phenethylamino-5,6-dimethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(isoxazol-5-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(isoxazol-5-yl)-4-phenethylamino-6-trifluoromethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-phenethylamino-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-phenethylamino-5-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-phenethylamino-5,6,7,8-tetrahydro-[1]-benzylthienothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-phenethylamino-5,6-cyclopentenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-phenethylamino-5,6-cycloheptenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-phenethylamino-6-ethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-phenethylamino-6-chlorothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-phenethylamino-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-phenethylamino-6-nitrothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-phenethylamino-5,6-dimethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyrazin-2-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyrazin-2-yl)-4-phenethylamino-6-trifluoromethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-phenethylamino-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-phenethylamino-5-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-phenethylamino-5,6,7,8-tetrahydro-[1]-benzylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-phenethylamino-5,6-cyclopentenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-phenethylamino-5,6-cycloheptenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-phenethylamino-6-ethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-phenethylamino-6-chlorothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-phenethylamino-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-phenethylamino-6-nitrothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-phenethylamino-5,6-dimethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-2-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyridin-2-yl)-4-phenethylamino-6-trifluoromethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-phenethylamino-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-phenethylamino-5-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-phenethylamino-5,6,7,8-tetrahydro-[1]-benzylthieno-[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6-cyclopentenothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-phenethylamino-5,6-cyclopentenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6-cycloheptenothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-phenethylamino-5,6-cycloheptenothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-ethylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-phenethylamino-6-ethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-chlorothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-phenethylamino-6-chlorothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5-chloro-6-methylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-phenethylamino-5-chloro-6-methylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-nitrothieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-phenethylamino-6-nitrothieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-5,6-dimethylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-phenethylamino-5,6-dimethylthieno[2,3-d]pyrimidine;

with 4-chloro-2-(pyridin-4-yl)-6-trifluoromethylthieno[2,3-d]pyrimidine gives 2-(pyridin-4-yl)-4-phenethylamino-6-trifluoromethylthieno[2,3-d]pyrimidine.

EXAMPLE 5

A solution of 2-(imidazol-1-yl)-6-methyl-4-(3-nitrobenzylamino)thieno-[2,3-d]pyrimidine in methanol is hydrogenated in the presence of Raney nickel. The catalyst is filtered off, and the solution is evaporated. Recrystallisation gives 2-(imidazol-1-yl)-6-methyl-4-(3-aminobenzylamino)thieno-[2,3-d]pyrimidine.

EXAMPLE 6

1 ml of freshly distilled acetaldehyde is added to a solution of 6 g of 2-(imidazol-1-yl)-6-methyl-4-(3-aminobenzylamino)thieno[2,3-d]pyrimidine and 0.5 g of titanium tetrachloride in 100 ml of methanol. 4 g of sodium cyanoborohydride are subsequently added, and the mixture is stirred for 30 hours. Semiconcentrated hydrochloric acid is added, and the mixture is subjected to conventional work-up, giving 2-(imidazol-1-yl)-6-methyl-4-(3-N-ethylaminobenzylamino)thieno[2,3-d]pyrimidine.

EXAMPLE 7

The following compounds are obtained analogously to Example 2

2-(imidazol-1-yl)-5,6,7,8-tetrahydro-4-(3,4-difluorobenzylamino)-[1]-benzylthieno[2,3-d]pyrimidine, m.p. 212°;
2-(imidazol-1-yl)-5,6-cyclopenteno-4-benzylaminothieno[2,3-d]pyrimidine, m.p. 221°;
2-(imidazol-1-yl)-6-methyl-4-benzylaminothieno[2,3-d]pyrimidine, m.p. 241°;
2-(imidazol-1-yl)-6-methyl-4-(3,4-dimethoxybenzylamino)thieno-[2,3-d]pyrimidine, m.p. 217°;
2-(imidazol-1-yl)-6-chloro-5-methyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine, m.p. 250°;
2-(imidazol-1-yl)-5,6,7,8-tetrahydro-4-benzylamino-[1]-benzylthieno-[2,3-d]pyrimidine, m.p. 190°;
2-(1,2,4-triazol-1-yl)-6-methyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine, m.p. 231°;
2-(imidazol-1-yl)-6-isopropyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine, m.p. 192°;
2-(imidazol-1-yl)-6-propyl-4-(3,4-methylenedioxybenzylamino)thieno-[2,3-d]pyrimidine, m.p. 183°.

EXAMPLE 8

The following compounds are obtained analogously to Example 2

2-(morpholin-4-yl)-4-(3,4-methylenedioxybenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine, m.p. 175°;
2-(morpholin-4-yl)-4-(3,4-methylenedioxybenzylamino)-5,6-dimethylthieno[2,3-d]pyrimidine, m.p. 140°;
2-(morpholin-4-yl)-4-(3-chloro-4-methoxybenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine,
2-(morpholin-4-yl)-4-(3-chloro-4-methoxybenzylamino)-5,6-dimethylthieno[2,3-d]pyrimidine,
2-(morpholin-4-yl)-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]-pyrimidine,
2-(morpholin-4-yl)-4-(3,4-methylenedioxybenzylamino)-6-ethylthieno-[2,3-d]pyrimidine, m.p. 217°;
2-(4-methylpiperazin-1-yl)-4-(3,4-methylenedioxybenzylamino)-6-ethylthieno[2,3-d]pyrimidine, m.p. 213°;
2-(4-methylpiperazin-1-yl)-4-(3,4-methylenedioxybenzylamino)-5,6-dimethylthieno[2,3-d]pyrimidine,
2-[4-(2-hydroxyethyl)piperazin-1-yl]-4-(3,4-methylenedioxybenzylamino)-5,6,7,8-tetrahydro-[1]-benzylthieno[2,3-d]pyrimidine, m.p. 243°;
2-(4-hydroxypiperidin-1-yl)-5,6-cyclopenteno-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine, m.p. 136-138°;
2-[4-(2-hydroxyethyl)piperazin-1-yl]-5,6-cyclopenteno-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine, decomposition 241°;
2-[4-(2-hydroxyethyl)piperazin-1-yl]-4-(3-chloro-4-methoxybenzylamino)-5,6-dimethylthieno[2,3-d]pyrimidine, m.p. 274°.

Pharmacological Test Results

Inhibition
Inhibition

of TIE-2
of RAF

Formula
IC₅₀(nmol/l)
IC₅₀(μmol)

150

4.3

5.3

Use Of Thienopyrimidines

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