Synthesis of 6 - substituted pyrimidine from ortic acid

Abstract

In the view of the extensive biological activities of various 6-substilUted uraeiis and related pyrimidine derivative~, a facile method for the synthesis of a number of 6- disuostitu(ed pyrimidines were developed (Schelne-I). 2,4-Dichloro pyrimidine -6-carbonyJ chloride 2 Vias synthesi;.<edby rdluxing Orotic acid I with phosphorus oxychloride and phosphorus pentaehloride. Compound 2 undem'ent substitution reaction with different substituted aromatic mnines to give 2, 4 - DiehIoro - 6- substituted phenylamido pyrimidine 10-14. 2, 4 _ Dichloro - 6- substituted phcnylamido pyrimidines were convcrted to the corresponding dimethoxy pyrimidine 15.19 on treatment with sodium methoxide in methanol. The demethylation reaction was attempted by renuxing 2. 4- dimethoxy phenylamido pyrimidine 15-19 wilh 6N hydrochloric acid gave the desired products 6-substituted pyrimidine 20-24. The structures of the synthesized products wcn; established from their analytical und spectroscopic duta.