Heterocyclic studies. Part XXXIII. Cleavage of 1,3-dimethylpyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione by nucleophiles

Abstract

Primary amines reacted with 1,3-dimethylpyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione to yield 5-alkyliminomethyl-6-amino-1,3-dimethyluracil derivatives. Hydrazine, 1,1-dimethylhydrazine, and hydroxylamine reacted in analogous fashion to give the hydrazone, dimethylhydrazone, and oxime, respectively, of 6-amino-5-formyl-1,3-dimethyluracil. Secondary and tertiary amines and methoxyamine failed to cleave the pyrimidopyrimidine.