Phenol → HCID 17854614, compound

HRID 1182572Notes

Reaction equation

HRID 1182572 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[Cl:10][C:11]1[CH:12]=[C:13]([C:18]2[C:23]([C:24]([NH:26][CH2:27][CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:25])=[C:22]([CH3:36])[N:21]=[C:20](S(C)(=O)=O)[N:19]=2)[CH:14]=[C:15]([Cl:17])[CH:16]=1>CN(C=O)C>[Cl:10][C:11]1[CH:12]=[C:13]([C:18]2[C:23]([C:24]([NH:26][CH2:27][CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:25])=[C:22]([CH3:36])[N:21]=[C:20]([O:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:19]=2)[CH:14]=[C:15]([Cl:17])[CH:16]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 17854585HCID 17854585, compound

Product 1

HCID 17854614HCID 17854614, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

39.3 mg (0.0798 mmol) of phenol was dissolved in DMF. 16.7 mg (0.418 mmol) of sodium hydride (60% oily substance) was added at 0° C. and stirred at the same temperature for 30 minutes. 100 mg (0.209 mmol) of 4-(3,5-dichlorophenyl)-6-methyl-2-methylsulfonyl-N-(3-phenylpropyl)-5-pyrimidinecarboxamide was added at the same temperature and stirred heating to room temperature for 12 hours. After concentration under reduced pressure, the obtained residue was diluted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1 to 1/1) to obtain the title compound.

Workup

  1. stirringstirred
  2. concentrationAfter concentration under reduced pressure
  3. additionthe obtained residue was diluted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1 to 1/1)

Sources & evidence

ORD record
ord-ab785c96ae4b46ad96fd8a5bb30ec577
Source dataset
uspto-grants-2007_10
Patent number
US07288544B2

Reaction notes

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