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

HRID 1182558Notes

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].C[NH:26][C:27](=[NH:29])[SH:28].S([O-])([O-])(=O)=O.[C:35]([O-])(=O)C.[Na+]>CN(C=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:29]=[C:27]([S:28][CH3:35])[N:26]=2)[CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 100 °C

Procedure

413 mg (1.21 mmol) of 2-acetyl-3-(3-chlorophenyl)-N-(3-phenyl-2-propen-1-yl) acrylamide was dissolved in 10 ml of DMF. 269 mg (0.968 mmol) of methylisothiourea-sulfate and 149 mg of (1.82 mmol) of sodium acetate were added thereto at room temperature and stirred at 100° C. for 2 days. DMF was evaporated under reduced pressure, and the residue 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 residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1) to obtain the title compound.

Workup

customDMF was evaporated under reduced pressure
additionthe residue was diluted with ethyl acetate
washwashed with saturated aqueous sodium chloride solution
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record: ord-5c03afcce54b4ce1b6392c96e6722a5a
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07288544B2

Reaction notes

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