Potassium Carbonate → HCID 67185034, 화합물

HRID 1020022노트

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HRID 1020022 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 67185034HCID 67185034, 화합물수율 76.3%

시약·촉매·용매 1

HCID 18180031Water 1,2-dimethoxyethane용매

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온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9130db1354c945d6b1471ff2d8871419
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716296B2

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