GB587559A - Manufacture of pyrimidine compounds - Google Patents

Abstract

Pyrimidine derivatives of the general formula <FORM:0587559/IV/1> wherein X and Y represent hydrogen or hydrocarbon radicals (but not both hydrogen), Z represents an alkylmercapto group and Am represents an arylamino group which may be unsubstituted or may bear one or more nonacidic substituents, e.g. halogen atoms, nitro, cyano or esterified carboxyl groups or hydrocarbon radicals (which themselves may bear substituents and which may be attached to the arylamino group directly or through an oxygen, nitrogen or sulphur atom or a sulphonyl or carbonyl group), are manufactured by the interaction of a 2-alkylmercapto-4-chloro- or -bromo-pyrimidine, bearing the atoms or groups X and Y in the 6- and 5-positions, with an arylamine, e.g. by heating the reagents together, preferably in the presence of a solvent or diluent (e.g. glacial acetic acid or aqueous acetone) and of an acid catalyst (e.g. hydrochloric acid). The corresponding 2-hydroxy compounds are obtained by heating the products with a mineral acid optionally in the present of a solvent. Examples describe the interaction of 2 - methylmercapto - 4 - chloro - 6 - methylpyrimidine with p-chloraniline, p-toluidine, p-anisidine and 6-bromo-2-naphthylamine, and of 4 - chloro - 2 - ethylthio - 5 : 6 - dimethyl - pyrimidine with p-chloraniline, and the conversion of certain of the products to the 2-hydroxy compounds by heating with aqueous hydrobromic acid or with concentrated hydrochloric acid and b - ethoxyethanol. Specification 587,550 is referred to.