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Lithium hydroxide, monohydrate → (R)-3-bromo-N-(2,4-dimethoxybenzyl)-1-(4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 62466
Notes
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Reaction equation

HRID 62466 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=2[O:21][CH3:22])[N:4]([C@@H:23]2[CH2:31][CH2:30][CH2:29][C:28]3[N:27](S(C4C=CC(C)=CC=4)(=O)=O)[N:26]=[CH:25][C:24]2=3)[N:3]=1.O[Li].O>C1COCC1>[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=2[O:21][CH3:22])[N:4]([C@@H:23]2[CH2:31][CH2:30][CH2:29][C:28]3[NH:27][N:26]=[CH:25][C:24]2=3)[N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 90303936(R)-3-bromo-N-(2,4-dimethoxybenzyl)-1-(1-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 90304068(R)-3-bromo-N-(2,4-dimethoxybenzyl)-1-(4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amineYield 92.3%

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent

Conditions

Temperature
60 °C

Procedure

To a solution of (R)-3-bromo-N-(2,4-dimethoxybenzyl)-1-(1-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (400 mg, 0.626 mmol) in THF (6.3 mL) was added 1N LiOH.H2O (105 mg, 2.504 mmol), then the mixture was stirred for 8 h at 60° C. Removed the solvent under reduced pressure and extracted with DCM and the combined organic layer was washed with water, brine and dried over anhydrous Na2SO4. The organic layer was concentrated in vacuo and the residue (R)-3-bromo-N-(2,4-dimethoxybenzyl)-1-(4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (280 mg, yield 92.3%) was used directly to next step.

Workup

  1. customRemoved the solvent under reduced pressure
  2. extractionextracted with DCM
  3. washthe combined organic layer was washed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-21dfcf73380a4ef8a2fc1effe2d8518a
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09446130B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes