Aluminium lithium hydride → HCID 67184148, compound

Participants

Reaction Steps

Lithium aluminium hydride (1 M in THF, 68.2 mmol, 10 eq) was added to a solution of 3-[4-pyridin-4-yl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazol-3-yl]-benzonitrile (2.57 g, 6.82 mmol) in dry THF (45.0 mL) under nitrogen and the reaction mixture was stirred at reflux for 3 hours. The reaction was cooled down in an ice bath and distilled water was added dropwise followed by a 1M NaOH solution (7.5 ml). The organic layer was removed under vacuum and DCM was added (30 ml) to the water phase. The dichloromethane layer was washed with brine and dried over Na2SO4. The filtrate was evaporated to dryness to give an oil, which was purified over silica gel, using DCM/MeOH/NH4OH (9.8:0.2:0.05) as eluent, to afford 3-[4-pyridin-4-yl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazol-3-yl]-benzylamine (1.48 g, 3.90 mmol, 56%).

Provenance & Evidence