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

반응식

[Br:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.O[CH2:10][C:11]1[S:12][CH:13]=[CH:14][CH:15]=1.C(OC(OCC(C)(C)C)N(C)C)C(C)(C)C>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[N:6]([CH2:10][C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)[CH:7]=1

참가 물질

실험 절차

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).