GB646070A - Manufacture of pyrimidylmercapto-carboxylic acids and derivatives thereof - Google Patents

Abstract

4-Oxypyrimidyl-(2)-mercaptocarboxylic acids of the general formula <FORM:0646070/IV (b)/1> (wherein R represents a hydrocarbon radical of 2-7 carbon atoms, e.g. an alkyl or aralkyl radical, and A represents a divalent aliphatic hydrocarbon radical of 1-4 carbon atoms, especially a methylene group), and salts, esters and amides thereof, are manufactured by reacting a 2-mercapto-4-oxypyrimidine of the general formula <FORM:0646070/IV (b)/2> with a halogencarboxylic acid Hal.A.COOH or a salt, ester or amide thereof, preferably in the presence of a diluent and an acid-binding agent, or by reacting a b - ketocarboxylic ester RCOCH2COOR1 (wherein COOR1 represents an esterified carboxyl group) with a pseudothiourea of the formula <FORM:0646070/IV (b)/3> or a salt, ester or amide thereof, or with thiourea and a halogencarboxylic acid Hal.A.COOH or a salt, ester or amide thereof, preferably in the presence of aqueous alkali. Esters obtained by the foregoing processes may be hydrolysed, whilst acids obtained by the foregoing processes or by hydrolysis of the esters may be esterified or converted into salts, which in turn may be converted into salts with other bases, e.g. sodium salts may be treated with calcium chloride to form calcium salts. Salts may also be formed with physiologically active bases, e.g. 2-aminothiazole. The products are useful as therapeutic agents (e.g. in hyperthyreosis) or intermediates therefor. Specified starting materials, some of which are employed in examples, are: 2-mercapto-4-oxy-6-ethyl-, -n-propyl-, -isopropyl-, -n-butyl-, -isobutyl-, -tert.-butyl- and -benzyl-pyrimidine; propionyl-, butyryl-, n-valeryl-, isovaleryl-, g : g : g -trimethylaceto- and g -phenylaceto-acetic esters; chloracetic, a - and b -bromopropionic, a -bromo-n- and -iso-butyric and a -bromoisovaleric acids and their salts, esters (e.g. ethyl esters) and amides; carboxymethyl-pseudo-thiourea.