Chlorotrimethylsilane → HCID 22842029, compound

Participants

Reaction Steps

To a stirred suspension of 2'-deoxy-5-ethynyluridine (J. Med. Chem., 26(5), 661-6, (1983)) (0.4 g, 1.6 mmol) in dry acetonitrile (15 ml) and chlorotrimethyl silane (0.7 ml, 5.6 mmol) was added, with ice cooling, triethylamine (1.13 ml, 8.1 mmol) and stirring was maintained at room temperature for 2.5 hr. Toluoylchloride (0.3 ml, 2.1 mmol) was then added and after stirring for a further 7 hr the mixture was filtered, the filtrate evaporated to dryness and the residue dissolved in ethanol (20 ml). Glacial acetic acid was then added and after stirring for 0.5 hr at room temperature the solvent was evaporated and residual acetic acid coevaporated with ethanol. Purification of the product by thick layer silica chromatography eluting with methanol/methylenechloride (1:24) followed by recrystallisation from methanol afforded title compound (0.03 g) melting at 176-9° C.

Provenance & Evidence