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

HRID 432223

Reaction equation

HRID 432223 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

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):

Workup

  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)

Sources & evidence

ORD record
ord-f2e73de560fb4b53bf2f7e63cdd1bbb7
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Linked notes

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