Water → 3-[3-(2-Bromo-2-methoxyethoxycarbonylethenyl)-4-chlorophenyl]-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine

HRID 1978854Notes

Reaction equation

HRID 1978854 reaction equation
[CH3:1][O:2][CH2:3][CH2:4]Br.[Br:6][C:7]([C:29]([OH:31])=[O:30])=[CH:8][C:9]1[CH:10]=[C:11]([N:16]2[C:21](=[O:22])[CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[N:18]([CH3:27])[C:17]2=[O:28])[CH:12]=[CH:13][C:14]=1[Cl:15].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:6][C:7]([C:29]([O:31][CH2:4][CH2:3][O:2][CH3:1])=[O:30])=[CH:8][C:9]1[CH:10]=[C:11]([N:16]2[C:21](=[O:22])[CH:20]=[C:19]([C:23]([F:26])([F:24])[F:25])[N:18]([CH3:27])[C:17]2=[O:28])[CH:12]=[CH:13][C:14]=1[Cl:15]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 865837973-[3-(2-Bromo-2-carboxyethenyl)-4-chlorophenyl]-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine

Product 1

HCID 865837963-[3-(2-Bromo-2-methoxyethoxycarbonylethenyl)-4-chlorophenyl]-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.52 ml of methoxyethyl bromide was added to a solution of 2.27 g of 3-[3-(2-bromo-2-carboxyethenyl)-4-chlorophenyl]-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine and 0.76 g of potassium carbonate in dimethylformamide, and the resulting solution was stirred for 17 hours. Thereafter, 100 ml of water were added and the aqueous phase was extracted with twice 100 ml of dichloromethane. The combined organic phases were washed with three times 50 ml of water, dried over sodium sulfate and evaporated down. After flash chromatography (dichloromethane→9:1 dichloromethane/ethyl acetate), the title compound was obtained as an oil.

Workup

  1. extractionthe aqueous phase was extracted with twice 100 ml of dichloromethane
  2. washThe combined organic phases were washed with three times 50 ml of water
  3. dry with materialdried over sodium sulfate
  4. customevaporated down

Sources & evidence

ORD record
ord-114c1d770a8943d2b14aa562839d3948
Source dataset
uspto-grants-2001_05
Patent number
US06239074B1

Reaction notes

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