Ethyl Acetate → 6-(2-Aminoethoxymethyl)-4-(3-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid (3,3-diphenylpropyl)amide

HRID 24611Notes

Reaction equation

HRID 24611 reaction equation
C(OCC)(=O)C.[C:7]1([CH:13]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:14][CH2:15][NH:16][C:17]([C:19]2[CH:20]([C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[CH:34]=3)[NH:21][C:22](=[O:32])[NH:23][C:24]=2[CH2:25][O:26][CH2:27][CH2:28][N:29]=[N+]=[N-])=[O:18])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>[H][H].[Pd]>[C:40]1([CH:13]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:14][CH2:15][NH:16][C:17]([C:19]2[CH:20]([C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[CH:34]=3)[NH:21][C:22](=[O:32])[NH:23][C:24]=2[CH2:25][O:26][CH2:27][CH2:28][NH2:29])=[O:18])[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 207588816-(2-Azidoethoxymethyl)-4-(3-chlorophenyl)-2-oxo-1,2, 3,4-tetrahydropyrimidine-5-carboxylic acid (3,3-diphenylpropyl)amide

Product 1

HCID 207588796-(2-Aminoethoxymethyl)-4-(3-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid (3,3-diphenylpropyl)amide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 178418361HCID 178418361, compoundSolvent

Procedure

10 ml of ethyl acetate was added to a mixture of 180 mg (0.330 mmol) of 6-(2-azidoethoxymethyl)-4-(3-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid (3,3-diphenylpropyl)amide 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 filtrate was concentrated under reduced pressure. The residue was purified by the basic silica gel chromatography (dichloromethane/methanol=100/1 to 20/1) to obtain the title compound.

Workup

  1. filtrationThe catalyst was filtered out
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by the basic silica gel chromatography (dichloromethane/methanol=100/1 to 20/1)

Sources & evidence

ORD record
ord-9a4aec40c46f4999a0faa280453aa97f
Source dataset
uspto-grants-2005_02
Patent number
US06855716B2

Reaction notes

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