The action of alkali on some pyrimidines and their derivatives

Abstract

Thymine and 1-substituted thymines were completely stable when treated with N-potassium hydroxideat 100° for 1 hr. Uracil was also shown to be stable, but 1-substituted uracils underwent ring fission to give urea and ammonia. Urea was found to give ammonia under these conditions. Cytosine derivatives were deaminated to different extents, depending on the nature of the 1-substituent, to give the corresponding 1-substituted uracil derivatives. No breakage of the 1-substituent bond in the cytosine derivatives was detected. Syntheses of 1-(p-nitrobenzyl)cytosine and 1-(p-nitrobenzyl)uracil are described.