Aluminium lithium hydride → 2-Aminomethyl-5-(2-cyclopropylmethylamino-thiazol-4-yl)-pyridine

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Reaction Steps

Add lithium aluminum hydride (75 mg, 2.0 mmol) portionwise over 1 minute to a solution of 5-(2-cyclopropylmethylamino-thiazol-4-yl)-pyridine-2-carbonitrile (340 mg, 1.3 mmol) in THF (20 mL) at room temperature under a nitrogen atmosphere. Stir the mixture for 10 min at room temperature. Quench the mixture successively with water (0.1 mL) and 1N NaOH (0.1 mL). Add sodium sulfate to absorb residual water, filter through Celite®, wash with DCM (30 mL) and concentrate in vacuo. Purify the residue by chromatography on silica gel (12 g) eluting with DCM/2M ammonia in methanol (97:3) to obtain the title compound (180 mg, 52%). MS (ES+) m/z: 261.3 (M+H)+.

Provenance & Evidence