Sodium Acetate → 4-(3-chlorophenyl)-6-methyl-N-(3-phenyl-2-propen-1-yl)-2-(pyridine-3-yl)-5-pyrimidinecarboxamide

HRID 1182559Notes

Reaction equation

HRID 1182559 reaction equation
[C:1]([C:4](=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1)[C:5]([NH:7][CH2:8][CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:6])(=O)[CH3:2].Cl.[C:26]([C:29]1[CH:30]=[NH+:31][CH:32]=[CH:33][CH:34]=1)(=[NH:28])[NH2:27].C([O-])(=O)C.[Na+]>CN(C=O)C.C(OCC)(=O)C>[Cl:24][C:20]1[CH:19]=[C:18]([C:17]2[C:4]([C:5]([NH:7][CH2:8][CH:9]=[CH:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:6])=[C:1]([CH3:2])[N:28]=[C:26]([C:29]3[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=3)[N:27]=2)[CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 541391202-acetyl-3-(3-chlorophenyl)-N-(3-phenyl-2-propene-1-yl)acrylamideHCID 178479320HCID 178479320, compound

Product 1

HCID 690728664-(3-chlorophenyl)-6-methyl-N-(3-phenyl-2-propen-1-yl)-2-(pyridine-3-yl)-5-pyrimidinecarboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

100 mg (0.294 mmol) of 2-acetyl-3-(3-chlorophenyl)-N-(3-phenyl-2-propen-1-yl) acrylamide was dissolved in 5 ml of DMF. 60.1 mg (0.381 mmol) of 3-amidinopyridinium hydrochloride and 28.9 mg of (0.353 mmol) of sodium acetate were added thereto and stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The obtained residue was stirred at 120° C. overnight, cooled down at room temperature and purified by the silica gel chromatography (hexane/ethyl acetate=1/2) to obtain the title compound.

Workup

  1. washwashed with saturated aqueous sodium chloride solution
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. stirringThe obtained residue was stirred at 120° C. overnight
  5. temperaturecooled down at room temperature
  6. custompurified by the silica gel chromatography (hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-048e1674beff47e49d8514b2ae055d62
Source dataset
uspto-grants-2007_10
Patent number
US07288544B2

Reaction notes

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