Claims
- 1. A process for the preparation of substituted pyrimidines of formula IA whereinR3 and R4 each independently represent a hydrogen atom, alkyl optionally substituted by phenyl, halogen, nitro, cyano, hydroxyl, C1-4-alkoxy, C1-4-haloalkoxy or C1-4-alkoxycarbonyl, or represents phenyl optionally substituted by halogen, nitro, cyano, hydroxyl, C1-4-alkyl, C1-4alkoxy, C1-4-haloalkyl, C1-4-haloalkoxy C1-4-haloalkylthio or halosulfanyl, and R1 represents C3-8 cycloalkyl optionally substituted by phenyl, halogen, nitro, cyano, amino, hydroxyl, C1-4-alkoxy, C1-4-haloalkoxy or C1-4-alkoxycarbonyl, or represents pyrazin-2-yl optionally substituted by halogen, nitro, cyano, amino, hydroxyl, C1-4-alkyl, C1-4-alkoxy, C1-4-haloalkyl, C1-4-haloalkoxy C1-4-haloalkylthio or halosulfanyl, R5 represent a halogen atom or a haloalkyl or haloalkoxy group and W-V represents N—CH, S—CH, N—CH—CH, CH—CH—CH or N—N(R6), in which R6 represents a C1-4 alkyl group which comprises reacting an amidine of formula II, or a salt thereof with 3,3-dichloroacrolein in an inert solvent, in the presence of a base and in the presence of a compound of formula IVH—X—R2 (IV), wherein X denotes oxygen and R2 represents a group and which further comprises perparing the 3,3-dichloroacrolein by an in-situ hydrolysis of a 1,1,1,3-tetrachloro-3-alkoxypropane.
- 2. A compound of formula IA whereinR3 and R4 each independently represent a hydrogen atom, alkyl optionally substituted by phenyl, halogen, nitro, cyano, hydroxyl, C1-4-alkoxy, C1-4-haloalkoxy or C1-4-alkoxycarbonyl, or represent phenyl optionally substituted by halogen, nitro, cyano, amino, hydroxyl, C1-4-alkyl, C1-4-alkoxy, C1-4-haloalkyl, C1-4-haloalkoxy C1-4-haloalkylthio or halosulfanyl, and R1 represents C3-8 cycloalkyl optionally substituted by phenyl, halogen, nitro, cyano, amino, hydroxyl, C1-4-alkyl, C1-4-alkoxy, C1-4-haloalkoxy or C1-4-alkoxycarbonyl, or represents pyrazin-2-yl optionally substituted by halogen, nitro, cyano, hydroxyl, C1-4-alkyl, C1-4-alkoxy, C1-4-haloalkyl, C1-4-haloalkoxy, C1-4-haloalkylthio or halosulfanyl, R5 represents a halogen atom or a haloalkyl or haloalkoxy group, and W-V represents N—CH, S—CH, N—CH—CH, CH—CH—CH or N—N(R6), in which R6 represents a C1-4 alkyl group.
Parent Case Info
This application is a division of application Ser. No. 09/547,666 filed Apr. 12, 2000, now U.S. Pat. No. 6,281,358, which claims the benefit of Provisional application Ser. No. 60/129,462, Apr. 15, 1999, and claims the benefit of Provisional application Ser. No. 60/139,356, filed Jun. 15, 1999.
US Referenced Citations (7)
Number |
Name |
Date |
Kind |
3498984 |
Santilli et al. |
Mar 1970 |
A |
4824949 |
Lachhein et al. |
Apr 1989 |
A |
4831138 |
Lachhein |
May 1989 |
A |
4831139 |
O'Murchu |
May 1989 |
A |
5824624 |
Kleeman et al. |
Oct 1998 |
A |
5840892 |
Bessard et al. |
Nov 1998 |
A |
5849758 |
Kleeman et al. |
Dec 1998 |
A |
Foreign Referenced Citations (4)
Number |
Date |
Country |
WO 9006918 |
Jun 1990 |
WO |
WO 9830549 |
Jul 1998 |
WO |
WO 9840379 |
Sep 1998 |
WO |
WO 9856789 |
Dec 1998 |
WO |
Non-Patent Literature Citations (3)
Entry |
J. Medwid et al., “Preparation of Triazolo [1,5-c] pyridines as Potential Dichlorides and Antiasthma Agents”, J. Med. Chem. 1990 33, 1230-1241. |
W. Schroth et al., “Synthesis of 1,3-thiazine-6-thiones From Formylketene Dichlorides and Thioamides”, Z. Chem. 24 (1984), 435-436. |
Chemical Abstracts, 103 : 6290 (1985). |
Provisional Applications (2)
|
Number |
Date |
Country |
|
60/129462 |
Apr 1999 |
US |
|
60/139356 |
Jun 1999 |
US |