GB581345A - Manufacture of pyrimidine compounds - Google Patents

Abstract

2 - Arylguanidino - 4 - hydroxypyrimidines, wherein either or both of the 5- and 6-positions may be unoccupied or may be occupied by a hydrocarbon radical or alternatively the 5- and 6-positions jointly may be occupied by a single divalent aliphatic hydrocarbon radical which forms with the 5- and 6-carbon atoms an alicyclic ring, and wherein the aryl radical may be substituted by one or more non-acidic substituents, are made by the reaction of an appropriate primary arylamine with an appropriate 2-cyanamino-4-hydroxypyrimidine. The aryl radical may be substituted, e.g. by hydrocarbon radicals (which themselves may be substituted and may be attached to the aryl radical directly or through an oxygen, nitrogen or sulphur atom or a sulphonyl or carbonyl group), halogen atoms, cyano, nitro, amino, acylamino or esterified carboxyl groups. Reaction may be effected by heating the 2-cyanamino-4-hydroxypyrimidine with the arylamine or a salt thereof, optionally in presence of a solvent or diluent, e.g. a mixture of b -ethoxyethanol and water. In examples (1) to (11), 2 - cyanamino - 4 - hydroxy - 6 - methylpyrimidine and aniline, p- or m-chloro-, p-nitro-, p-cyano-, p-methylmercapto-, p-phenyl-, p-iodo-, 3 : 5-dichloro- or 3 : 4-dimethyl-aniline or b -naphthylamine react to give the corresponding 2 - arylguanidino - 4 - hydroxy - 6 - methylpyrimidines. In examples (12) to (17), p-chloroaniline and the 2-cyanamino-4-hydroxy derivatives of 5 : 6-trimethylene-, 5 : 6-dimethyl-, 5-phenyl-or 5-ethyl-6-methyl-pyrimidine or of 5 : 6 : 7 : 8-tetrahydroquinazoline or of pyrimidine react to give the corresponding 2 - p - chlorophenyl - guanidine - 4 - hydroxypyrimidine derivatives. Specification 581,334 is referred to. Specifications 581,346 and 581,347 also are referred to in the first Provisional Specification. 2 - Cyanamino - 4 - hydroxypyrimidines used as starting materials above are made by the reaction of dicyandiamide with a formylacetic ester appropriately substituted if necessary on the a - and/or b -carbon atoms.