Reaction #52875

Reaction equation

4-(3-chlorophenyl)-6-[(2-cyclohexylethoxy)methyl]-2-phenyl-1,4-dihydropyrimidine-5-carboxylic acid

cinnamylamine

WSC hydrochloride

HOBT

→

title compound

4-(3-chlorophenyl)-6-[(2-cyclohexylethoxy)methyl]-2-phenyl-5-[(3-phenyl-2-propene-1-yl)- carbamoyl]-1,4-dihydropyrimidine

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   Temperatureunder cooling with ice, and they
2. 2
   Washwashed with saturated aqueous sodium hydrogencarbonate solution
3. 3
   DryingThe organic layer was dried over anhydrous sodium sulfate
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   OtherThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1 to 1/1)

Procedure

110 mg (0.243 mmol) of 4-(3-chlorophenyl)-6-[(2-cyclohexylethoxy)methyl]-2-phenyl-1,4-dihydropyrimidine-5-carboxylic acid and 38.8 mg (0.292 mmol) of cinnamylamine were dissolved in 10 ml of dichloromethane. 69.9 mg (0.365 mmol) of WSC hydrochloride and 37.2 mg (0.243 mmol) of HOBT were added to the obtained solution under cooling with ice, and they were stirred at room temperature for 3 hours. The reaction mixture was diluted with dichloromethane and then washed with saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous sodium 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.

Source