5,5-Dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione → 2-amino-3-(4-chlorophenyl)-N-(2,2-diethoxyethyl)-N-isopropylpropionamide

HRID 1670498Notes

Reaction equation

HRID 1670498 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH:24]C(=O)OCC=C)[C:10](=[O:23])[N:11]([CH2:15][CH:16]([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])[CH:12]([CH3:14])[CH3:13])=[CH:4][CH:3]=1.CC1(C)C(=O)NC(=O)NC1=O>C(Cl)Cl>[NH2:24][CH:9]([CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[C:10]([N:11]([CH2:15][CH:16]([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])[CH:12]([CH3:14])[CH3:13])=[O:23]

Participants

4

Reactant 2

HCID 905095,5-Dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrioneHCID 86597579Allyl {2-(4-chlorophenyl)-1-[(2,2-diethoxyethyl)isopropylcarbamoyl]ethyl}carbamate

Product 1

HCID 673416462-amino-3-(4-chlorophenyl)-N-(2,2-diethoxyethyl)-N-isopropylpropionamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10 mg of palladium tetrakistriphenylphosphine are added to a solution of 13.2 g of allyl {2-(4-chlorophenyl)-1-[(2,2-diethoxyethyl)isopropylcarbamoyl]ethyl}carbamate, 18.9 g of dimethylbarbituric acid in 140 ml of methylene chloride under a protective argon gas atmosphere, and the reaction mixture is stirred for 12 h at room temperature. The reaction solution is concentrated under reduced pressure and purified by flash chromatography on silica gel (eluent methylene chloride, 1% Et3N, 0-10% methanol). The desired product is obtained with MW=356.90 (calculated monoisotopic); measured value (M−C2H6O+H)+: 311.10

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure
  2. custompurified by flash chromatography on silica gel (eluent methylene chloride, 1% Et3N, 0-10% methanol)

Sources & evidence

ORD record
ord-0525ccb1ade64faaba70a13542282546
Source dataset
uspto-grants-2011_08
Patent number
US07994168B2

Reaction notes

Loading…