Imidazole → HCID 22878324, compound

Participants

Reaction Steps

To a solution of 3'-O-t-butyldimethylsilyl-5'-deoxy-5'-hydroxymethyl thymidine prepared according to the method of Example 5 (0.3 g, 0.9 mmol) in dry acetonitrile (5 ml) and ether (3.4 ml) were added 3 eq of triphenyl phosphine (0.7 g, 2.8 mmol), 4 eq of imidazole (0.3 g, 3.7 mmol) and 2.2 eq of iodine (0.5 g, 2.8 mmol). The reaction mixture was stirred for 45 min and the solvent was evaporated. Ethyl acetate was added to the residue and the residue washed with water, saturated sodium chloride and dried with sodium sulfate. The title compound was purified by flash chromatography using a 30-50% gradient of ethyl acetate in hexane. The yield was 90%.

Provenance & Evidence