GB712595A - New pyrimidines and processes for their production - Google Patents

Abstract

The invention comprises pyrimidine derivatives, having amoebicidal activity, of the general formula <FORM:0712595/IV (b)/1> and their salts, wherein Z represents a monovalent primary, secondary or tertiary amino radical, and X and X1 are the same or different and are hydrogen or chlorine or a methoxy, amino, nitro or cyano radical. Z is preferably a dialkyl amino radical in which the alkyl group contains from 1 to 5 carbon atoms, a piperidino, hexamethyleneimino or pyrrolidino radical. The compounds may be obtained (a) by reacting ammonia or a primary or secondary amine with a derivative of the formula <FORM:0712595/IV (b)/2> where Hal is halogen and R is hydrogen or an acyl radical; (b) by reacting ammonia with a derivative of the formula <FORM:0712595/IV (b)/3> (c) when Z represents -NH2, by reacting ammonia with the correspondingly 5-substituted 2,4,6-trihalogeno-pyrimidine or 2-amino- or 2-acetamido-4,6-dihalogenopyrimidine; or (d) by introducing one or more substituents at X and X1 of a 2,4,6-triamino-5-phenylpyrimidine. In methods (a) and (b), the reaction is effected above 150 DEG C. in the presence of a solvent such as ethanol. In the examples: (1) 2,4-diamino-5 - (41 - chlorophenyl) - 6 - di - n - butylamino - pyrimidine is prepared by heating di-n-butyl-amine with 2,4-diamino-5-(41-chlorophenyl)-6-chloropyrimidine in ethanol in an autoclave: by similar methods are prepared:-(2) the 6-dimethylamino, (3) the 6-diethylamino, (4) the 6-di-n-propylamino, (5) the 6-n-butylamino, (6) the 6-piperidino, (7) the 6-hexamethylene-imino, (8) the 6-pyrrolidino and (9) the 6-di-n-pentylamino derivatives and (10) 2,4-diamino-5-(31,41 - dichlorophenyl) - 6 - di - n - butylamino-pyrimidine: (11) 2,4,6-triamino-5-(41-chlorophenyl)-pyrimidine is prepared from ammonia and 2 - acetamido - 4,6 - dichloro - 5 - (41 - chlorophenyl)-pyrimidine: (12) 2,4,6-triamino-5-phenyl-pyrimidine is prepared from ammonia and 2,4-diamino-5-phenyl-6-chloropyrimidine and is converted into the 5-(41-nitrophenyl) derivative by the action of potassium nitrate in conc. sulphuric acid; by reduction of this nitro derivative with Adams platinum catalyst, 2,4,6 - triamino - 5 - (41-aminophenyl) - pyrimidine is formed and may be converted into the 5-(41-cyanophenyl) derivative by Sandmeyer's reaction: (13) the monohydrochloride of 2,4-diamino - 5 - phenyl - 6 - di - n - butylamino pyrimidine is prepared by adding to dry HCl in ether the product obtained by heating di-n-butylamine with 2,4-diamino-5-phenyl-6-chloropyrimidine; nitrating as in (12) yields the 5-(41-nitrophenyl) derivative: (14) the product of example (1) is obtained by heating ammonia with 2 - amino - 4 - chloro - 5 - (41 - chlorophenyl) - 6 - di - n - butylamino-pyrimidine, which itself is obtained by heating excess di-n-butylamine with 2-acetamido-4,6-dichloro-5-(41 - chlorophenyl) - pyrimidine. Specification 710,070 is referred to.