GB671926A - Improvements relating to the preparation of 4-aminopyrimidine compounds - Google Patents

Abstract

2 - Thiol - 4 - amino - pyrimidine compounds of the general formula <FORM:0671926/IV (b)/1> are prepard by condensing a 2,4-dithiopyrimidine of the general formula <FORM:0671926/IV (b)/2> where R is hydrogen or an alkyl or aryl group, or an aryl group substituted by chlorine, bromine or alkyl groups with ammonia or a primary or secondary amine of the general formula <FORM:0671926/IV (b)/3> wherein R1 is hydrogen or an alkyl, aryl or aralkyl group, a hydroxyalkyl group or a dialkylaminoalkyl group, containing in each case not more than 20 carbon atoms, R2 is hydrogen or methyl or R1 and R2 together form the arms of a cyclic system such as piperidine or morpholine. The dithiopyrimidine derivatives may be obtained by the process of Specification 598,514. The amine is preferably employed in excess. Examples describe the preparation of (1) 2-thiol-4-methyl-aminopyrimidine from dithiouracil and methylamine; (2) 2-thiol-4-tetradecylamino-pyrimidine from dithiouracil and tetradecylamine. Similarly from dithiouracil and the corresponding amine are prepared: (3) 2-thiol-4-n-amylaminopyrimidine; (4) 2-thiol-4-benzyl-aminopyrimidine; (5) 2-thiol-4-b -hydroxyethylaminopyrimidine; (6) 2-thiol-4-b -diethylaminoethyl aminopyrimidine; (7) 2-thiol-4-(N-piperidino) pyrimidine; (8) 2-thiol-4-(4-morpholino) pyrimidine; (9) 2-thiol-4-N-methylpiperazinopyrimidine; (10) 2-thiol-4-dimethylaminopyrimidine; (12) 2-thiol-4-anilinopyrimidine; (13) 2 - thiol - 4 - p - chloranilinopyrimidine; (16) 2 - thiol - 4 - p - methoxy - anilinopyrimidine; (17) 2-thiol-4-methylanilino-pyrimidine; (18) 2-thiol-4-amino-pyrimidine from dithiouracil and ammonia; (19) 2-thiol-4-(diphenylmethyl) aminopyrimidine; (20) 2-thiol-4- (b -morpholinoethyl) aminopyrimidine; (21) 2-thiol - 4 - n - propyl - methylaminopyrimidine. Further examples describe the preparation from the appropriate 6-substituted dithiouracil of (11) 2 - thiol - 6 - methyl - 4 - anilinopyrimidine; (14) 2 - thiol - 6 - methyl - 4 - n - amylaminopyrimidine; (15) 2-thiol-6-phenyl-4-n-amylpyrimidine; (22) 2-thiol-6-methyl-4-aminopyrimidine; (23) 2-thiol-6-methyl-4-piperidinopyrimidine. A sample has been furnished under Sect. 2 (5) of 2-thiol-4(31-methoxypropylamino)-6-p-chlorophenylpyrimidine, prepared by reacting 6-p-chlorophenyl thiouracil with 3-methoxy-propylamine. Specification 671,927 also is referred to.