反应详情

温度

80 °C

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):

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)