Potassium Carbonate → HCID 67185034, compound

HRID 1020022Notes

Reaction equation

HRID 1020022 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1B(O)O.[CH2:14]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH2:27][CH:26]([C:30](=[O:39])[NH:31][C:32]2[CH:37]=[C:36](Cl)[N:35]=[CH:34][N:33]=2)[CH2:25]1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.O>[CH2:14]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH2:27][CH:26]([C:30](=[O:39])[NH:31][C:32]2[CH:37]=[C:36]([C:4]3[C:3]([O:2][CH3:1])=[CH:8][CH:7]=[CH:6][C:5]=3[O:9][CH3:10])[N:35]=[CH:34][N:33]=2)[CH2:25]1)=[O:23])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2734343(2,6-Dimethoxyphenyl)boronic acidHCID 86645892HCID 86645892, compound

Product 1

HCID 67185034HCID 67185034, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2,6-dimethoxyphenyl boronic acid (0.60 g, 3.3 mmol) in a mixture of dimethoxyethane/water (8 ml, 3:1), 3-(6-chloro-pyrimidin-4-ylcarbamoyl)-piperidine-1-carboxylic acid benzyl ester (0.82 g, 2.2 mmol) was added followed by tetrakis(triphenylphospine) palladium(0) (0.15 g, 0.13 mmol) and saturated solution of potassium carbonate (2 ml). The reaction mixture was heated at 90° C. for 2 h, then it was cooled to room temperature and filtered through a celite bed which was washed with ethyl acetate. The aqueous layer was extracted with ethyl acetate, the organic layers were combined, washed with brine, dried (Na2SO4) and evaporated under reduced pressure. The crude product was purified by column chromatography, using hexane/ethyl acetate (4:1) as eluent, to provide 0.80 g (yield: 53%) of 3-[6-(2,6-dimethoxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester.

Workup

  1. additionwas added
  2. temperatureit was cooled to room temperature
  3. filtrationfiltered through a celite bed which
  4. washwas washed with ethyl acetate
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated under reduced pressure
  9. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-9130db1354c945d6b1471ff2d8871419
Source dataset
uspto-grants-2014_05
Patent number
US08716296B2

Reaction notes

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