2-(Iodomethyl)oxirane → HCID 20475702, compound

Participants

Reaction Steps

A mixture of 5-chloropyrimidine-2-thione (6.9 mmol) and potassium tert-butoxide (6.9 mmol) was stirred together in anhydrous DMF (40 ml) for 5 min before epiiodohydrin (6.9 mmol) was added. The mixture was stirred at 80° C. for 7 h while small portions of potassium tert-butoxide were added from time to time to maintain a strong basic solution. The solvent was then removed at reduced pressure, the residue triturated with water (50 ml), the insoluble material extracted with chloroform and the dried (MgSO4) chloroform solution evaporated leaving the oily sulfide, yield 29%. This material was chromatographically homogenous and was identified by its spectroscopic properties. 1H NMR (CDCl3): δ2.6-3.4 (5H, m), 8.50 (H-4, H-6).

Provenance & Evidence