Sodium hydride → HCID 22030560, compound

HRID 454322Notes

Reaction equation

HRID 454322 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:13]=[CH:12][C:7]2[N:8]=[C:9]([CH3:11])[NH:10][C:6]=2[CH:5]=1.Cl[C:15]1[C:24]2[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][N:16]=1>CN(C=O)C.O>[CH3:26][O:25][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][C:21]=1[O:27][CH3:28])[N:18]=[CH:17][N:16]=[C:15]2[O:3][C:4]1[CH:13]=[CH:12][C:7]2[N:8]=[C:9]([CH3:11])[NH:10][C:6]=2[CH:5]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 133725342-Methyl-1H-benzimidazol-6-ol

Product 1

HCID 22030560HCID 22030560, compoundYield 48.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (71 mg, 1.8 mmol) was added to 5-hydroxy-2-methylbenzimidazole (204 mg, 0.89 mmol) in anhydrous DMF (2.5 ml) under an argon atmosphere. The mixture was stirred at ambient temperature for 10 minutes. 4-Chloro-6,7-dimethoxyquinazoline (200 mg, 0.89 mmol) was added and the reaction mixture stirred at 95° C. for 2 hours. Upon cooling to ambient temperature the mixture was poured in water and extracted with ethyl acetate. The organic phase was washed with brine, dried (MgSO4), silica was added and the solvent evaporated off. The obtained powder was placed on the top of a disposable silica column (ISOLUTE) and the product eluted off using a gradient of methanol/dichloromethane (3/97, 5/95, 8/92). Evaporation of the solvent gave 6,7-dimethoxy-4-(2-methyl-1H-benzimidazol-6-yloxy)quinazoline (145 mg, 48%).

Workup

  1. stirringthe reaction mixture stirred at 95° C. for 2 hours
  2. temperatureUpon cooling to ambient temperature the mixture
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried (MgSO4), silica
  6. additionwas added
  7. customthe solvent evaporated off
  8. washthe product eluted off
  9. customEvaporation of the solvent

Sources & evidence

ORD record
ord-d0e181f278e5410db06fffe674098b6a
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

Loading…