Synthesis of 1‐(2‐deoxy‐2‐fluoro‐β‐D‐arabinofuranosyl)‐5‐iodo [2‐14C] uracil

Abstract

AbstractThe synthesis of the title compound (7) is described. [2‐14C] cytosine (1) is treated with an aqueous mixture of sodium bisulfite and sodium sulfate at 80°C for 30 min. The resulting solid is then treated with aqueous sodium hydroxide and passed through a cation exchange column, producing [2‐14C] uracil (2). Iodionation with iodic acid and iodine in acetic acid yielded 5‐iodo‐[2‐14C]uracil (3) Treatment of (3) with hexamethyldisilazane formed the trimethylsilated pyrimidine. Condensation with 3‐0‐acetyl‐5‐0‐benzoyl‐2‐deoxy‐2‐fluoro‐D‐arabinosyl bromide produced a mixture of α, β isomes. Separation by column chromatography and saponification with aqueous potassium carbonate yielded the title compound.