Imidazole → 3'-O-t-butyldimethylsilyl-5'-iodo-5'-deoxythymidine

Participants

Reaction Steps

To a stirred solution of the thymidine iodide (8.0 g, 24.7 mmol) prepared according to the method of Example 24 in dry DMF, was added imidazole (4.2 g, 61.7 mmol). After 5 minutes tert-butyldimethyl silyl chloride (4.47 g, 29.64 mmol) was added and the mixture stirred for 4 hours. The reaction mixture was then diluted with ethyl acetate (250 ml), washed with water (2×100 ml) and brine (50 ml) and then dried with sodium sulfate. The title compound was purified by flash chromatography using 60% ethyl acetate in hexane in 92% yield.

Provenance & Evidence