2-Thiophenemethanol → 5-Bromo-1-(2-thienylmethyl)pyrimidin-2-one

Participants

Reaction Steps

5-Bromopyrimidin-2-one (10 mmol), 2-hydroxymethylthiophene (36 mmol) and N,N-dimethylformamide dineopentyl acetal (15 mmol) in DMF (40 ml) were heated together at 80° C. for 150 min. The coloured solution was evaporated to dryness at reduced pressure (1 mmHg), the residual viscous material triturated with pet, ether (2×25 ml) and with ether (50 ml) when it solidified. This material was dissolved in chloroform and chromatographed on alumina (20 g, activity III). The title compound was eluted with chloroform; yield 48%, m.p. 188°-190° C. (EtOAc). 1H NMR (TFA) δ 5.68 (CH2); 7.18, 7.41, 7.58 (H3', H4', H5'), 8.95 (H4, H6).

Provenance & Evidence