1-(Bromomethyl)-4-chlorobenzene → 4-(4-chlorobenzylthio)pyrimidin-2(1H)-one

Reaction equation

C[O-].[Na+].[NH:4]1[CH:11]=[CH:10][C:8](=[S:9])[NH:7][C:5]1=[O:6].Br[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1>CO>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][S:9][C:8]2[CH:10]=[CH:11][NH:4][C:5](=[O:6])[N:7]=2)=[CH:15][CH:16]=1

Participants

Procedure

Sodium methoxide (0.057 g, 1.050 mmol) was added to a mixture of 4-thiouracil (0.128 g, 1.0 mmol) and 1-(bromomethyl)-4-chlorobenzene (0.216 g, 1.05 mmol) in 1 mL MeOH. After stirring the reaction at RT overnight, the reaction mixture was concentrated, partitioned between EtOAc and sat. NH4Cl. The organic phase was dried (MgSO4), concentrated and the residue was subjected to ISCO flash chromatography (silica gel/methylene chloride to 80:20 methylene chloride-MeOH gradient) to afford 4-(4-chlorobenzylthio)pyrimidin-2(1H)-one 2A (0.17 g, 0.673 mmol, 67% yield) as a light yellow solid. 1H NMR (400 MHz, methanol-D) δ 7.58 (1H, d, J=6.78 Hz), 7.43 (2H, d, J=8.53 Hz), 7.30 (2H, d, J=8.53 Hz), 6.39 (1H, d, J=6.78 Hz), 4.44 (2H, s).