Aluminium lithium hydride → 2-(3-(1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl)-2-methylpropan-1-amine

HRID 384053Notes

Reaction equation

HRID 384053 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][C:9]([C:10]3[CH:11]=[C:12]([C:16]([CH3:20])([CH3:19])[C:17]#[N:18])[CH:13]=[CH:14][CH:15]=3)=[C:4]2[CH:3]=[N:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][C:9]([C:10]3[CH:11]=[C:12]([C:16]([CH3:20])([CH3:19])[CH2:17][NH2:18])[CH:13]=[CH:14][CH:15]=3)=[C:4]2[CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 426348322-(3-(1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl)-2-methylpropanenitrile

Product 1

HCID 579696542-(3-(1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl)-2-methylpropan-1-amineYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-(3-(1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl)-2-methylpropanenitrile (22 mg, 0.084 mmol) was added slowly a 2 M solution of lithium aluminium hydride (167.70 ml, 0.336 mmol) in tetrahydrofuran (3 ml). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was allowed to cool down to room temperature and was partitioned between water and ethyl acetate. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 μM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were freeze-dried to give the title compound as a white solid (12 mg, 54% yield).

Workup

  1. temperatureto cool down to room temperature
  2. customwas partitioned between water and ethyl acetate
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 μM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]
  7. customThe fractions were freeze-dried

Sources & evidence

ORD record
ord-eebcd08150e741358b29b66f855a71e6
Source dataset
uspto-grants-2013_02
Patent number
US08367697B2

Reaction notes

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