Ethyl Acetate → 4-(3-Chlorophenyl)-3-(3,3-diphenylpropylcarbamoyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid

HRID 24614Notes

Reaction equation

HRID 24614 reaction equation
C(OCC)(=O)C.[Cl:7][C:8]1[CH:9]=[C:10]([CH:14]2[C:19]([C:20]([O:22]CC3C=CC=CC=3)=[O:21])=[C:18]([CH3:30])[NH:17][C:16](=[O:31])[N:15]2[C:32](=[O:49])[NH:33][CH2:34][CH2:35][CH:36]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:11]=[CH:12][CH:13]=1>[H][H].[Pd]>[Cl:7][C:8]1[CH:9]=[C:10]([CH:14]2[C:19]([C:20]([OH:22])=[O:21])=[C:18]([CH3:30])[NH:17][C:16](=[O:31])[N:15]2[C:32](=[O:49])[NH:33][CH2:34][CH2:35][CH:36]([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 15546109Benzyl 4-(3-chlorophenyl)-3-(3,3-diphenylpropylcarbamoyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Product 1

HCID 225701354-(3-Chlorophenyl)-3-(3,3-diphenylpropylcarbamoyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 178418361HCID 178418361, compoundSolvent

Procedure

10 ml of ethyl acetate was added to a mixture of 141 mg (0.237 mmol) of benzyl 4-(3-chlorophenyl)-3-(3,3-diphenylpropylcarbamoyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate and a catalytic amount of 10% palladium/carbon, and they were stirred at room temperature in hydrogen atmosphere under normal pressure overnight. The catalyst was filtered out, and the obtained filtrate was concentrated under reduced pressure. The residue was washed with hexane/ethyl acetate (1/1) and then dried under reduced pressure to obtain the title compound.

Workup

  1. filtrationThe catalyst was filtered out
  2. concentrationthe obtained filtrate was concentrated under reduced pressure
  3. washThe residue was washed with hexane/ethyl acetate (1/1)
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-cd287b5f97f346d58ec07aa85d639907
Source dataset
uspto-grants-2005_02
Patent number
US06855716B2

Reaction notes

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