Potassium Hydroxide → HCID 178508618, compound

HRID 897523Notes

Reaction equation

HRID 897523 reaction equation
[N+](C1C=CC(C([O:10][C@H:11]2[CH2:14][C@H:13]([N:15]3[C:19]4=[N:20][CH:21]=[N:22][C:23]([NH2:24])=[C:18]4[C:17]([C:25]4[CH:30]=[CH:29][C:28]([O:31][C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)=[CH:27][CH:26]=4)=[N:16]3)[CH2:12]2)=O)=CC=1)([O-])=O.[OH-].[K+]>CO>[NH2:24][C:23]1[N:22]=[CH:21][N:20]=[C:19]2[N:15]([C@H:13]3[CH2:12][C@H:11]([OH:10])[CH2:14]3)[N:16]=[C:17]([C:25]3[CH:26]=[CH:27][C:28]([O:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:29][CH:30]=3)[C:18]=12

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 178508619HCID 178508619, compound

Product 1

HCID 178508618HCID 178508618, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of trans 3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]cyclobutyl 4-nitrobenzoate (0.081 g, 0.000164 mol) in methanol (5 mL) was reacted with potassium hydroxide (0.091 g, 0.00164 mol) at reflux for one hour. The solvent was removed in vacuo and the residue was partitioned between water (10 mL) and ethyl acetate (5 mL). The layers were separated and the water layer was extracted aqueous with ethyl acetate (2×5 mL). The combined organics were washed with 1 N aqueous sodium hydroxide (5 mL) and brine (5 mL). The organic layer was dried over magnesium sulfate, and the solvent was removed in vacuo. The residue was suspended in water and lyopholyzed to give trans 3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-cyclobutanol (0.055 g, 0.000147 mol) as a white solid.

Workup

  1. temperatureat reflux for one hour
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between water (10 mL) and ethyl acetate (5 mL)
  4. customThe layers were separated
  5. extractionthe water layer was extracted aqueous with ethyl acetate (2×5 mL)
  6. washThe combined organics were washed with 1 N aqueous sodium hydroxide (5 mL) and brine (5 mL)
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c0a146b0eaca4d68a45096edeb2db833
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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