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

HRID 2059843Notes

Reaction equation

HRID 2059843 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

5

Reactant 3

HCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 27343944-ThiouracilHCID 10942334Sodium Methoxide

Product 1

HCID 1785185414-(4-chlorobenzylthio)pyrimidin-2(1H)-oneYield 67.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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).

Workup

  1. customthe reaction at RT overnight
  2. concentrationthe reaction mixture was concentrated
  3. custompartitioned between EtOAc and sat. NH4Cl
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-97c8fe6b452443bbbf7ba5d97a2f46e1
Source dataset
uspto-grants-2012_10
Patent number
US08278316B2

Reaction notes

Loading…