Benzoyl chloride → HCID 22842024, compound

Participants

Reaction Steps

To a stirred suspension of 2'deoxy-5-ethynyluridine (J. Med. Chem., 26(5), 661-6, (1983)) (0.3 g, 1.19 mmoles) in dry acetonitrile (8 ml) and chlorotrimethylsilane (0.5 ml) was added, with ice cooling, triethylamine (0.85 ml, 6.1 mmoles) and the whole was stirred at room temperature for 2 hrs. Benzoylchloride (0.18 ml, 1.54 mmoles) was then added and the mixture stirred for a further 1.5 hrs and filtered. The filtrate was concentrated, the residue dissolved in ethanol (10 ml) and glacial acetic acid (0.4 g) was added. After stirring for 0.5 hr, the solvents were evaporated and the residue purified by column chromatography on silica gel eluting with methylene chloride/methanol (19:1) to give the title compound 0.2 g (47% yield) melting at 156°-7° C.

Provenance & Evidence