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

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Reaction Steps

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

Provenance & Evidence