Synthesis of 5 - bromo - 6 - amido uracil from Orotic acid

Abstract

In the view of the extensive biological activities of various 5 and 6. substituted uracils and related pyrimidine derivatives, a facile method for the synthesis of a number of 5, 6.disubstituted pyrimidines were developed (Seheme-l). 2, 4-Dichloropyrimidine-&.carbonyl chloride 2 was synthesized by refluxing Orotic acid 1 with phosphorus oxychloride and phosphorus pentachloride. Compound.2 underwent substitute rbaction with different substituted aromatic amines to give 2, 4 - Dichloro . 6. substituted pbenylamido pyrimidine 9-14. 2, 4 - dichloro - &. substituted phenylamido pyrimidines were converted to the correspondin~ dimethoxy pyrimi.dine 15-19 on treatment with sodium methoxide in methanol. The bromination reaction was attempted by several methods but only NBSI TFA.TFAA method gave the desired products 20-23. The structures of the synthesized products were established from their analytical and spectroscopic data. ....................................................................................