Water → HCID 19702761, compound

HRID 861298Notes

Reaction equation

HRID 861298 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]([CH3:20])[C:10]2=[O:21])=[C:4]([CH2:22][C:23]([CH3:25])=[CH2:24])[C:3]=1[OH:26].C(=O)([O-])[O-].[K+].[K+].Br[CH2:34][C:35]([O:37][CH3:38])=[O:36].O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:18])([F:19])[F:17])[N:11]([CH3:20])[C:10]2=[O:21])=[C:4]([CH2:22][C:23]([CH3:25])=[CH2:24])[C:3]=1[O:26][CH2:34][C:35]([O:37][CH3:38])=[O:36]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 152799451-[4-Chloro-6-fluoro-3-hydroxy-2-(2-methyl-2-propenyl)phenyl]-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dione

Product 1

HCID 19702761HCID 19702761, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

First, 1.0 g of 1-[4-chloro-6-fluoro-3-hydroxy-2-(2-methyl-2-propenyl)phenyl]-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dione was dissolved in 15 ml of N,N-dimethylformamide, to which 0.43 g of potassium carbonate and 0.4 ml of methyl bromoacetate were added, and the mixture was stirred at room temperature for 30 minutes. After completion of the reaction, the reaction mixture was poured into water and extracted with diethyl ether. The organic layer was dried and concentrated. The residue was subjected to silica gel chromatography, which afforded 1.0 g of 1-[4-chloro-6-fluoro-3-methoxycarbonylmethyloxy-2-(2-methyl-2-propenyl)phenyl]-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dione.

Workup

  1. additionwere added
  2. customAfter completion of the reaction
  3. extractionextracted with diethyl ether
  4. customThe organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6ef8f576078948b4b96e15ba43a24526
Source dataset
uspto-grants-1998_02
Patent number
US05714437

Reaction notes

Loading…