A new Method for the Synthesis of 5-Benzyl-1-(2-Hydroxyethoxy Methyl)Uracil (Bau), A Potent Uridine Phosphorylase Inhibitor, And Its N₃-And N₁, N₃, -Substituted Analogs

Abstract

A new methodology for the synthesis of 5-benzyl-l-(2-hydroxyethoxymethyl)uracil (BAU)² (1), a potent uridine phosphorylase inhibitor, has been developed. The coupling of bis(trimethylsilyl) derivative of 5-benzyl uracil with 2-acetoxyethoxymethyl bromide, followed by removal of the protecting 0-acetyl group, afforded compound 1. However, treatment of the silyl derivatives of 5-benzyluracil with 2-acetoxyethyl acetoxymethyl ether in the presence of stannic chloride as catalyst, followed by deblocking, gave three products,1, 2 and 3, respectively.