Water → 2-Chloro-1-(6-chloropyrimidin-4-yl)-1H-benzimidazole

HRID 1968417Notes

Reaction equation

HRID 1968417 reaction equation
[Cl:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.[H-].[Na+].[Cl:13][C:14]1[CH:19]=[C:18](Cl)[N:17]=[CH:16][N:15]=1.O>CN(C=O)C>[Cl:1][C:2]1[N:6]([C:18]2[CH:19]=[C:14]([Cl:13])[N:15]=[CH:16][N:17]=2)[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 709434,6-DichloropyrimidineHCID 785722-Chlorobenzimidazole

Product 1

HCID 598224532-Chloro-1-(6-chloropyrimidin-4-yl)-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of 2-Chloro-1H-benzoimidazole (3.0 g, 19.67 mmol) in 10 mL DMF at 0° C. under argon atmosphere is added with sodium hydride (60% dispersion in mineral oil, 1.18 g, 29.5 mmol) portion wise. After 20 minutes, 4,6-dichloro-pyrimidine (3.3 g, 22.1 mmol) is added. The resulting reaction mixture is allowed to warm to room temperature and stirred overnight. The reaction mixture is treated with 120 mL water and extracted three times with 100 mL dichloromethane. The organic extracts are washed with brine and dried over MgSO4. Filtration and concentration under reduced pressure, followed by flash chromatography on silica gel (0% EtOAc/hexanes to 20% EtOAc/hexanes gradient), affords the title compound as a white powder: Rf=0.35 (20% EtOAc/hexanes); 1H NMR 400 MHz (DMSO-d6) δ 9.26 (s, 1H), 8.25 (s, 1H), 7.80-7.72 (m, 2H), 7.43-7.37 (m, 2H); MS m/z 265.1 (M+1).

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted three times with 100 mL dichloromethane
  3. washThe organic extracts are washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationFiltration and concentration under reduced pressure

Sources & evidence

ORD record
ord-e568ebdc73b04328a4bda51682383d86
Source dataset
uspto-grants-2013_04
Patent number
US08426404B2

Reaction notes

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