4-Nitrophenyl chloroformate → Benzyl 4-(3-chlorophenyl)-3-(3,3-diphenylpropylcarbamoyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

HRID 24612Notes

Reaction equation

HRID 24612 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])=[C:12]([CH3:24])[NH:11][C:10]([O:25]C)=[N:9]2)[CH:5]=[CH:6][CH:7]=1.ClC(O[C:31]1[CH:36]=[CH:35][C:34]([N+]([O-])=O)=[CH:33][CH:32]=1)=O.[C:40](=[O:43])([O-])O.[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])=[C:12]([CH3:24])[NH:11][C:10](=[O:25])[N:9]2[C:40](=[O:43])[NH:11][CH2:12][CH2:13][CH:8]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:4]2[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 821294-Nitrophenyl chloroformateHCID 516892Sodium BicarbonateHCID 22570191Benzyl 4-(3-chlorophenyl)-2-methoxy-6-methyl-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 15546109Benzyl 4-(3-chlorophenyl)-3-(3,3-diphenylpropylcarbamoyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

558 mg (1.50 mmol) of benzyl 4-(3-chlorophenyl)-2-methoxy-6-methyl-1,4-dihydropyrimidine-5-carboxylate and 364 mg (1.81 mmol) of p-nitrophenyl chloroformate were dissolved in 10 ml of dichloromethane. 1 ml of saturated sodium hydrogencarbonate solution was added to the obtained solution at 0° C., and they were stirred at room temperature for 24 hours. The reaction mixture was diluted with dichloromethane and then washed with water and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The product was washed with ether and then dried under reduced pressure to obtain the title compound.

Workup

  1. washwashed with water and saturated aqueous sodium chloride solution
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. washThe product was washed with ether
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-83ed804ac4aa4f27bcc24ff251f42e34
Source dataset
uspto-grants-2005_02
Patent number
US06855716B2

Reaction notes

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