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

HRID 432223

反応式

HRID 432223 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

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):

後処理

  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)

出典と根拠

ORDレコード
ord-f2e73de560fb4b53bf2f7e63cdd1bbb7
出典データセット
uspto-grants-2003_12
特許番号
US06660744B1

関連ノート

読み込み中…