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

HRID 24610Notes

Reaction equation

HRID 24610 reaction equation
C(OCC)(=O)C.[C:7]1([CH2:13][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:7]1([CH2:13][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:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 207588806-(2-Azidoethoxymethyl)-4-(3-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid (3-phenylpropyl) amide

Product 1

HCID 207588786-(2-Aminoethoxymethyl)-4-(3-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid (3-phenylpropyl) amide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 178418361HCID 178418361, compoundSolvent

Procedure

10 ml of ethyl acetate was added to a mixture of 164 mg (0.350 mmol) of 6-(2-azidoethoxymethyl)-4-(3-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid (3-phenylpropyl)amide and a catalytic amount of 10% palladium/carbon, and they were stirred at room temperature in hydrogen atmosphere under normal pressure for 24 hours. 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-5a40b1a51b4843318d95d552070325ed
Source dataset
uspto-grants-2005_02
Patent number
US06855716B2

Reaction notes

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