Pyrimidine Derivatives and Related Compounds. XXX. : Synthesis and Some Reactions of 5, 6-Dicyano-1, 3-dimethyluracil

Abstract

5, 6-Dicyano-1, 3-dimethyluracil (1) was synthesized stepwise from 6-chloro-5-formyl-1, 3-dimethyluracil (2). Treatment of 1 with butylamine or aniline afforded 6-butylamino-(5) or 6-anilino-5-cyano-1, 3-dimethyluracil (6), respectively. 3-Amino-5, 7-dimethylpyrazolo [3, 4-d] pyrimidine-4, 6 (5H, 7H)-dione (7) was obtained by the reaction of 1 with hydrazine hydrate. When 1 was refluxed in methanol in the presence of a catalytic amount of sodium methoxide, 5-cyano-6-methoxy-1, 3-dimethyluracil (9) was obtained. Acid hydrolysis of 1 afforded 6-carbamoyl-1, 3-dimethylorotic acid (10).