Potassium Carbonate → HCID 15136875, compound

HRID 326530Notes

Reaction equation

HRID 326530 reaction equation
[F:1][C:2]([CH3:10])([CH3:9])[CH:3]([OH:8])[C:4]([O:6][CH3:7])=[O:5].[CH3:11][O:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[N:16]=[C:15](S(C)(=O)=O)[N:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:11][O:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[N:16]=[C:15]([O:8][CH:3]([C:2]([F:1])([CH3:10])[CH3:9])[C:4]([O:6][CH3:7])=[O:5])[N:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 1513687413152-61-9

Product 1

HCID 15136875HCID 15136875, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

4 g (26.6 mmol) Methyl 3-fluoro-2-hydroxy-3-methylbutanoate and 5.81 g (26.6 mmol) 4,6-dimethoxy-2-methylsulphonylpyrimidine were dissolved in 75 ml dimethylformamide at 20° C. and treated with 1.84 g (13.3 mmol) potassium carbonate. The suspension was stirred for 5 hours at 20° C. and heated for one hour at 60° C. The reaction mixture was then poured into 150 ml ice-water and extracted with three lots of 75 ml ethyl acetate. The combined ethyl acetate phase was washed with water, dried over magnesium sulphate, filtered and evaporated. The solid residue was purified by silica gel column chromatography using hexane/ethyl acetate as eluent.

Workup

  1. temperatureheated for one hour at 60° C
  2. extractionextracted with three lots of 75 ml ethyl acetate
  3. washThe combined ethyl acetate phase was washed with water
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customThe solid residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-01bd6c0cd67f45fc9cf48c929b517f25
Source dataset
uspto-grants-1993_12
Patent number
US05270289

Reaction notes

Loading…