Unfused heterobicycles as amplifiers of phleomycin. VI. Some thienyl- and thiazolyl-pyrimidines with strongly basic side chains

Abstract

2-Chloro-4-(thien-2'-yl)pyrimidine (2a) and its thiazol-2'-yl analogue (2d) are prepared by condensation of 2-chloropyrimidine with thien-2-yl- and thiazol-2-yl-lithium, followed by oxidation of the dihydro intermediates. 4-Chloro-6-methyl-2-(thien-2'-yl)pyrimidine (3b),its 2-(2',4'-dimethylthiazol-5'-yl) analogue (3f) and the 2-(2'-methylthiazol-4'-yl) analogue (4b) are made from the corresponding pyrimidinones, which are available by primary synthesis. Each chloro compound is converted by nucleophilic displacement into its β-dimethylaminoethylamino and β-dimethylaminoethylthio derivatives, for which activities as amplifiers of phleomycin are reported and discussed.