Aluminium lithium hydride → 2-(5-(1H-pyrazolo[3,4-b]pyridin-4-yl)thiophen-3-yl)-2-methylbutan-1-amine

HRID 44685Notes

Reaction equation

HRID 44685 reaction equation
[CH3:1][C:2]([C:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]3[NH:18][N:19]=[CH:20][C:13]=23)[S:9][CH:8]=1)([CH2:5][CH3:6])[C:3]#[N:4].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH:18]1[C:14]2=[N:15][CH:16]=[CH:17][C:12]([C:10]3[S:9][CH:8]=[C:7]([C:2]([CH3:1])([CH2:5][CH3:6])[CH2:3][NH2:4])[CH:11]=3)=[C:13]2[CH:20]=[N:19]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 666460942-methyl-2-[5-(1H-pyrazolo[3,4-b]pyridin-4-yl)-3-thienyl]butanenitrile

Product 1

HCID 498004942-(5-(1H-pyrazolo[3,4-b]pyridin-4-yl)thiophen-3-yl)-2-methylbutan-1-amineYield 8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A cooled solution of 2-methyl-2-[5-(1H-pyrazolo[3,4-b]pyridin-4-yl)-3-thienyl]butanenitrile (234 mg, 0.8287 mmol) in THF (10.00 mL) was treated with LiAlH4 in THF (1.658 mL of 2 M, 3.315 mmol) dropwise over a period of 3 minutes. The reaction was allowed to stir at RT overnight and then quenched with water whilst cooling. The mixture was extracted with EtOAc (2×) and the organics dried (MgSO4), filtered, concentrated and purified by column chromatography (70:9:1 DCM/MeOH/NH4OH) to give the product as a white solid (19.0 mg, 8% Yield). 1H NMR (DMSO, 400 MHz) δ 0.71 (3H, t), 1.25 (3H, s), 1.50-1.64 (1H, m), 1.70-1.84 (1H, m), 2.67 (1H, d), 2.79 (1H, d), 7.46-7.48 (2H, m), 7.89 (1H, s), 8.48 (1H, s), 8.50 (1H, d); MS (ES+) 287.09

Workup

  1. customquenched with water
  2. temperaturewhilst cooling
  3. extractionThe mixture was extracted with EtOAc (2×)
  4. dry with materialthe organics dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by column chromatography (70:9:1 DCM/MeOH/NH4OH)

Sources & evidence

ORD record
ord-15c702e1f1b54a348c81676292bb05ca
Source dataset
uspto-grants-2013_09
Patent number
US08541445B2

Reaction notes

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