2-Diethoxyethyl(dimethyl)(2-(2,4-diphenyl-5-pyrimidyl)-2-oxoethyl)ammonium bromide

Abstract

The title compound is a useful anthelmintic agent.

Description

This invention relates to chemical compounds. In particular it is concerned with a compound of the formula: ##STR1##

It is useful as an anthelmintic agent. When administered per os by gavage in an aqueous methyl cellulose suspension at a dose of about 100 mg/kg to mice harboring the pinworm syphacia obvelata, a 79% reduction of pinworm population is secured.

The method currently preferred for the preparation of the compound of this invention is briefly described as follows:

A. 2,4-diphenyl-5-pyrimidyl bromomethyl ketone

An 86 g (0.31 mole) portion of 2,4-diphenyl-5-pyrimidyl methyl ketone in 1.1 l. of dioxane was treated with 136 g (0.61 mole) of cupric bromide using rapid stirring. The reaction mixture was stirred for 15 hrs at ambient temperature, refluxed for 3 hrs, cooled, stirred for 2 additional hrs and filtered. The off-white solid was washed with two 300 ml portions of chloroform. The filtrate and washings were combined and concentrated to dryness under reduced pressure to give a gray crystalline solid.

The crude product was recrystallized from 2 l. of absolute ethanol. The off-white solid was washed with 200 ml of absolute ethanol and air dried, m.p. 131.degree.-133.degree.. Yield: 57 g (52%).

Anal. Calcd. for C.sub.18 H.sub.13 BrN.sub.2 O: C, 61.20; H, 3.31; N, 7.93. Found: C, 61.68; H, 3.68; N, 7.95.

B. 2-diethoxy(dimethyl)[2-(2,4-diphenyl-5-pyrimidyl)-2-oxoethyl] ammonium bromide

A 27.5 g (0.078 mole) portion of A in 300 ml benzene was treated with 12.6 (0.078 mole) of dimethylaminoacetaldehyde diethylacetal. The reaction mixture was refluxed for 5 hrs. The slurry was stirred overnight at room temperature and filtered. The white solid was washed with 150 ml of benzene and air dried, m.p. 98.degree.-108.degree.. Yield: 38 g (95%).

A 36 g portion of the crude product was recrystallized from 150 ml of acetone and air dried, m.p. 149.degree.-151.degree.. Yield: 28 g (70%).

An analytical sample, m.p. 152.degree.-154.degree., was recrystallized from acetone at 50 ml/g.

Anal. Calcd. for C.sub.26 H.sub.32 BrN.sub.3 O.sub.3 : C, 60.70; H, 6.27; N, 8.17. Found: C, 60.92; H, 6.43; N, 8.14.

Claims

1. 2-Diethoxyethyl(dimethyl)[2-(2,4-diphenyl-5-pyrimidyl)-2-oxoethyl]ammonium bromide.