Potassium Carbonate → 5-[2-(R)-Tetrahydropyranyloxyheptyloxy]-2-(4-benzyloxyphenyl)pyrimidine

HRID 485995ノート

反応式

HRID 485995 の反応式
[OH:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:10][CH:9]=2)=[N:6][CH:7]=1.S(C1C=CC(C)=CC=1)(O[CH2:26][C@H:27]([O:33][CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][O:35]1)[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[O:35]1[CH2:36][CH2:37][CH2:38][CH2:39][CH:34]1[O:33][C@H:27]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:26][O:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:12][CH:13]=2)=[N:6][CH:7]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 227174625-Hydroxy-2-(4-benzyloxyphenyl)pyrimidineHCID 86747620(R)-2-tetrahydropyranyloxyheptyl tosylate

生成物 1

HCID 678491895-[2-(R)-Tetrahydropyranyloxyheptyloxy]-2-(4-benzyloxyphenyl)pyrimidine収率 121.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

In a 500 ml four-necked flask were charged 12.2 g (43.7 mmol) of 5-hydroxy-2-(4-benzyloxyphenyl)pyrimidine, 24 g (65.5 mmol) of (R)-2-tetrahydropyranyloxyheptyl tosylate, 12 g of potassium carbonate, and 183 ml of DMF, and the mixture was stirred at 80° C. for 5 hours. After cooling, the reaction mixture was poured into 500 ml of ice-water and extracted with ethyl acetate. The extract was washed with water, and the solvent was removed by distillation under reduced pressure to obtain 28.6 g of a crude product, which was purified by silica gel column chromatography to obtain 25.3 g of the titled compound.

後処理

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. customthe solvent was removed by distillation under reduced pressure
  5. customto obtain 28.6 g of a crude product, which
  6. customwas purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-67e3832e51cf4097a650e3c83aadf71a
出典データセット
uspto-grants-1994_03
特許番号
US05290477

反応ノート

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