Water → HCID 14853369, compound

HRID 326526Notes

Reaction equation

HRID 326526 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]([OH:14])[C:10]([O:12][CH3:13])=[O:11])[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:21][O:22][C:23]1[CH:28]=[C:27]([O:29][CH3:30])[N:26]=[C:25](S(C)(=O)=O)[N:24]=1.O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]([O:14][C:25]2[N:26]=[C:27]([O:29][CH3:30])[CH:28]=[C:23]([O:22][CH3:21])[N:24]=2)[C:10]([O:12][CH3:13])=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 296017Methyl 2-hydroxy-2-(3-methoxyphenyl)acetateHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidine

Product 1

HCID 14853369HCID 14853369, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

8 g (230 mmol) Methyl 2-(3-methoxyphenyl)glycolate was dissolved in 100 ml dimethylformamide and treated with 2.8 g (20.4 mmol) potassium carbonate. After 20 minutes stirring, 8.8 g (40.7 mmol) 4,6-dimethoxy-2-methylsulphonylpyrimidine was added and the mixture heated for 1 hour at 90° C. The reaction mixture was then poured into 100 ml water and extracted with 100 ml ethyl acetate. The combined ethyl acetate phase was washed with water, dried over magnesium sulphate and evaporated. The residue was recrystallised from diisopropyl ether.

Workup

  1. extractionextracted with 100 ml ethyl acetate
  2. washThe combined ethyl acetate phase was washed with water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe residue was recrystallised from diisopropyl ether

Sources & evidence

ORD record
ord-bc4375d4267b4f8aaccffb8f37821d5f
Source dataset
uspto-grants-1993_12
Patent number
US05270289

Reaction notes

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