Sodium Carbonate Monohydrate → [2-(4-amino-1-cyclopentyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-5-phenoxyphenyl]methanol

HRID 432223노트

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HRID 432223 반응식
[CH:1]1([N:6]2[C:10]3=[N:11][CH:12]=[N:13][C:14]([NH2:15])=[C:9]3[C:8](I)=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[O:17]([C:24]1[CH:25]=[CH:26][C:27]2B(O)[O:30][CH2:29][C:28]=2[CH:33]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[NH2:15][C:14]1[N:13]=[CH:12][N:11]=[C:10]2[N:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[N:7]=[C:8]([C:27]3[CH:26]=[CH:25][C:24]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:33][C:28]=3[CH2:29][OH:30])[C:9]=12

참가 물질

6

반응물 3

HCID 2735133Sodium Carbonate MonohydrateHCID 223468081-cyclopentyl-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amineHCID 223468265-Phenoxy-1,3-dihydro-2,1-benzoxaborol-1-ol

생성물 1

HCID 22347383[2-(4-amino-1-cyclopentyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-5-phenoxyphenyl]methanol수율 60.9%

시약·촉매·용매 2

HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

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온도
80 °C

실험 절차

A mixture of 1-cyclopentyl-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.36 g, 0.0011 mol), 5-phenoxy-1,3-dihydro-2,1-benzoxaborol-1-ol (0.30 g, 0.0013 mol), tetrakis (triphenylphophine)palladium (0.077 g, 0.000067 mol) and sodium carbonate monohydrate (0.34 g, 0.0028 mol) in ethylene glycol dimethyl ether (7 mL) and water (5 mL) was heated at 80° C. under an atmosphere of nitrogen for seventeen hours. The mixture was allowed to cool to ambient temperature, and the solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate (20 mL) and aqueous saturated solution of sodium carbonate (20 mL). The aqueous layer was further extracted with ethyl acetate (3×20 mL). The organic solvent was removed under reduced pressure. Ethyl acetate (15 mL) was added to the residue and white precipitate was formed. The solid was filtered and washed with acetone (2×15 mL) and dichloromethane (1×15 mL) to yield [2-(4-amino-1-cyclopentyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-5-phenoxyphenyl]methanol (0.267 g, 0.00067 mol):

후처리

  1. temperatureto cool to ambient temperature
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was partitioned between ethyl acetate (20 mL) and aqueous saturated solution of sodium carbonate (20 mL)
  4. extractionThe aqueous layer was further extracted with ethyl acetate (3×20 mL)
  5. customThe organic solvent was removed under reduced pressure
  6. additionEthyl acetate (15 mL) was added to the residue
  7. customwhite precipitate was formed
  8. filtrationThe solid was filtered
  9. washwashed with acetone (2×15 mL) and dichloromethane (1×15 mL)

출처 및 근거

ORD 기록
ord-f2e73de560fb4b53bf2f7e63cdd1bbb7
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660744B1

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