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

HRID 485995노트

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HRID 485995 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-67e3832e51cf4097a650e3c83aadf71a
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05290477

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