REACTION OF URACIL NUCLEOSIDES WITH 1-METHYLIMIDAZOLE IN THE PRESENCE OF PHOSPHORYL CHLORIDE : A CONVENIENT METHOD FOR THE SYNTHESIS OF 4-SUBSTITUTED PYRIMIDIN-2 (1H)-ONE NUCLEOSIDES

抄録

Reaction of 2', 3', 5'-tri-O-benzoyluridine (3) with 1-methylimidazole in the presence of phosphoryl chloride in acetonitrile afforded 3-methyl-1-imidazolium intermediate (4), from which a variety of 4-substituted pyrimidin-2 (1H)-one ribosides (5-12) were obtained in a one-pot manner by nucleophilic substitutions under mild conditions. Application of this method to 2'-deoxyriboside of several pyrimidines (13a, b, c) is also described.