Cesium carbonate → 4-(4-methanesulfonyl-phenoxy)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidine

HRID 1931605노트

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HRID 1931605 반응식
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:19]1[N:24]=[CH:23][N:22]=[C:21]2[N:25]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][O:29]3)[N:26]=[CH:27][C:20]=12.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([O:11][C:19]2[N:24]=[CH:23][N:22]=[C:21]3[N:25]([CH:28]4[CH2:33][CH2:32][CH2:31][CH2:30][O:29]4)[N:26]=[CH:27][C:20]=23)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

참가 물질

6

반응물 4

HCID 10796Cesium carbonateHCID 1233504-(Methylsulfonyl)phenolHCID 2394984-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidineHCID 516892Sodium Bicarbonate

생성물 1

HCID 669152954-(4-methanesulfonyl-phenoxy)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidine수율 81.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

4-(Methylsulfonyl)-phenol (Oakwood Products, Inc., West Columbia, S.C., USA; 516 mg, 3 mmol) and cesium carbonate (1.63 g, 5 mmol) were added to a solution of 4-chloro-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidine (from Step 1; 610 mg, 2.56 mmol) in dimethylformamide (15 mL). The mixture was heated at 90° C. for 1 h, then cooled, poured into saturated aqueous sodium bicarbonate solution, and extracted three times with ethyl acetate. The combined organic extracts were washed with twice with water and once with brine, dried (magnesium sulfate), filtered, and evaporated to give 4-(4-methanesulfonyl-phenoxy)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidine (780 mg, 58%).

후처리

  1. temperaturecooled
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic extracts were washed with twice with water
  4. dry with materialonce with brine, dried (magnesium sulfate)
  5. filtrationfiltered
  6. customevaporated

출처 및 근거

ORD 기록
ord-95b0b34a792b48a6adc6666296382f00
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188098B2

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