Potassium Carbonate → HCID 14855645, compound

HRID 2051441Notes

Reaction equation

HRID 2051441 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C:12]2[C:17]([C:18]([OH:20])=[O:19])=[C:16]([F:21])[CH:15]=[CH:14][CH:13]=2)[N:4]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:34][Si:35]([CH3:40])([CH3:39])[CH2:36][CH2:37]O.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH3:10][O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([O:11][C:12]2[C:17]([C:18]([O:20][CH2:37][CH2:36][Si:35]([CH3:40])([CH3:39])[CH3:34])=[O:19])=[C:16]([F:21])[CH:15]=[CH:14][CH:13]=2)[N:6]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 180132-(Trimethylsilyl)ethanolHCID 682631,1'-CarbonyldiimidazoleHCID 4056919Benzoic acid, 2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]-6-fluoro-

Product 1

HCID 14855645HCID 14855645, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-(4,6-dimethoxypyrimidin-2-yl)oxy-2-fluorobenzoic acid (3.0 g) and carbonyldiimidazole (1.8 g) were dissolved in 50 ml of tetrahydrofuran, and the mixture was refluxed under heating and stirring for one hour. After cooling the reaction solution, 2-(trimethylsilyl)ethanol (6.0 g) and potassium carbonate (1.5 g) were added thereto, and the mixture was refluxed under heating and stirring for one hour. The reaction solution was poured into ice water and extracted with ethyl ether. The extract was washed with water and dried. Then, the solvent was evaporated under reduced pressure. The residue thereby obtained was purified by silica gel column chromatography to obtain the above identified compound as a pale yellow oily substance (2.4 g).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating
  3. additionwere added
  4. temperaturethe mixture was refluxed
  5. temperatureunder heating
  6. stirringstirring for one hour
  7. extractionextracted with ethyl ether
  8. washThe extract was washed with water
  9. customdried
  10. customThen, the solvent was evaporated under reduced pressure
  11. customThe residue thereby obtained
  12. customwas purified by silica gel column chromatography
  13. customto obtain the

Sources & evidence

ORD record
ord-733de14673574a51868443423f03f818
Source dataset
uspto-grants-1991_05
Patent number
US05019151

Reaction notes

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