Potassium Acetate → 3'-Fluorothymidine

Participants

Reaction Steps

To a solution of 3.22 g (10 millimoles) 3'-deoxy-3'-fluoro-5'-mesylthymidine in 10 ml N,N-dimethylformamide, was added 1.96 g (20 millimoles) potassium acetate, and the mixture was heated at 110°±5° C. for 60 minutes with stirring. The solvent was distilled off from the reaction mixture under reduced pressure, 30 ml water was added to the residue, and the mixture was extracted twice with 50 ml ethyl acetate. The extract was washed twice with 30 ml water and dried over anhydrous sodium sulfate, the solvent was distilled off from the dried extract under reduced pressure, and the residue was dissolved in methanol. This solution was decolorized by treatment with 1.4 g of activated charcoal, the decolorized solution obtained by filtering off the charcoal was concentrated, and the residue was treated with ammonia-saturated methanol and subjected to purification in the same way as in Example 1, giving 1.8 g (7.38 millimoles) of 3'-deoxy-3'-fluorothymidine as white, granular crystals. The yield was 73.8%.

Provenance & Evidence