N-Piperidinoethanol → HCID 10228358, compound

Participants

Reaction Conditions

Reaction Steps

185 mg (0.254 mmol) of 4-(3-chlorophenyl)-6-methyl-2-(methylthio)-N-(3-phenylpropyl)-5-pyrimidinecarboxamide was dissolved in 5 ml of dichloromethane. 87.7 mg (0.508 mmol) of mCPBA (m-chloroperbenzoic acid) was added thereto at 0° C. and stirred at the same temperature for 6 hours. 1 ml of saturated aqueous sodium bisulfite solution was added thereto at the same temperature and stirred for 30 minutes heating to room temperature. After the reaction mixture was diluted with dichloromethane, the organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The obtained residue was dissolved in 5 ml of DMF. Alkoxide prepared from 146 mg (1.13 mmol) of 1-piperidine ethanol and 45.2 mg (1.13 mmol) of sodium hydride (60% oily substance) was added at 0° C. and stirred heating to room temperature for 1 hour. 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 basic silica gel chromatography (hexane/ethyl acetate=5/1 to 1/1) to obtain the title compound.

Provenance & Evidence