Carbon tetrabromide → HCID 58774549, compound

Participants

Reaction Steps

To a solution of THF (20 mL) was added 0.63 (102, 1.56 mmol, 1 equiv) of 2-{4-[(3-bromophenyl)amino]-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-7-yl}ethanol, 0.82 g (3.12 mmol, 2 equiv) triphenylphosphine and 1.03 g (3.12 mmol, 2 equiv) carbon tetrabromide. The solution was stirred at rt for 1 h until completion and the reaction mixture was evaporated under reduced pressure. The resulting crude material was purified by flash chromatography eluting with 9:1 CH2Cl2/EtOAc yielding 396 mg (54%) of a light yellow solid. 1H-NMR (CDCl3-d) δ 8.52 (s, 1H), 7.94 (m, 1H), 7.58 (m, 1H), 7.24 (m, 2H), 7.10 (s, 1H), 3.56 (m, 2H), 3.15 (m, 2H), 3.03 (m, 1H), 2.57 (m, 1H), 2.19 (m, 2H), 2.04 (m, 2H), 1.68 (m, 1H); TLC Rf=0.30 (9:1 CH2Cl2/EtOAc); LCMS RT=3.92 min; [M+H]+=466.2.

Provenance & Evidence