Potassium Carbonate → HCID 67185034、化合物

HRID 1020022ノート

反応式

HRID 1020022 の反応式
[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

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 2734343(2,6-Dimethoxyphenyl)boronic acidHCID 86645892HCID 86645892、化合物

生成物 1

HCID 67185034HCID 67185034、化合物収率 76.3%

試薬・触媒・溶媒 1

HCID 18180031Water 1,2-dimethoxyethane溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9130db1354c945d6b1471ff2d8871419
出典データセット
uspto-grants-2014_05
特許番号
US08716296B2

反応ノート

読み込み中…