Water → HCID 86644404, compound

HRID 2194669Notes

Reaction equation

HRID 2194669 reaction equation
[C:1]1([C:7]2[NH:8][CH:9]=[C:10]([CH:12]=[O:13])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:17]1[N:22]=[CH:21][CH:20]=[CH:19][N:18]=1.O>CN(C)C=O>[C:1]1([C:7]2[N:8]([C:17]3[N:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH:9]=[C:10]([CH:12]=[O:13])[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 744042-ChloropyrimidineHCID 178519858HCID 178519858, compound

Product 1

HCID 86644404HCID 86644404, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-phenyl-1H-imidazole-4-carbaldehyde (700 mg) in dimethylformamide (30 mL) was added sodium hydride (60% in oil, 180 mg) at room temperature and the mixture was stirred for 30 min. 2-Chloropyrimidine (489 mg) was further added and the mixture was stirred for 15 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→2:3) to give the title compound as a yellow oil (yield 160 mg, yield 16%).

Workup

  1. stirringthe mixture was stirred for 15 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→2:3)

Sources & evidence

ORD record
ord-6a3aa8455efe469787cf6ffc1cc0e7e3
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

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