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Synthesis of 1‐(2‐deoxy‐2‐fluoro‐β‐D‐arabinofuranosyl)‐5‐iodo [2‐ 14 C] uracil
Author(s) -
Swigor J. E.,
Pittman K. A.
Publication year - 1985
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580220909
Subject(s) - chemistry , aqueous solution , uracil , saponification , sodium bisulfite , sodium hydroxide , potassium carbonate , sodium methoxide , nuclear chemistry , acetic acid , potassium hydroxide , sodium , sodium carbonate , bromide , inorganic chemistry , organic chemistry , methanol , dna , biochemistry
The synthesis of the title compound (7) is described. [2‐ 14 C] 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‐ 14 C] uracil (2). Iodionation with iodic acid and iodine in acetic acid yielded 5‐iodo‐[2‐ 14 C]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.