Aluminium lithium hydride → HCID 59811504, compound

Participants

Reaction Steps

A solution of [2-methyl-7-(2,4,6-trimethyl-phenyl)-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-yl]-carbamic acid tert-butyl ester (0.150 g, 0.40 mmol) dissolved in THF (3 mL) was treated with the slow addition of 1M lithium aluminum hydride in THF (0.80 mL, 0.80 mmol). The mixture was placed under a nitrogen atmosphere and heated to reflux for 8 h. The mixture was cooled to room temperature and the excess reagent was quenched by the dropwise addition of 10% potassium sodium tartrate solution. Ethyl acetate (40 mL) was added and washed sequentially with 10% Rochelle salt solution (40 mL) and brine (25 m), dried over magnesium sulfate, and evaporated. The residue was purified by silica gel chromatography eluting with ethyl acetate/hexane (3:2) to afford 0.056 g (48% yield) of methyl-[2-methyl-7-(2,4,6-trimethyl-phenyl)-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-yl]-amine (5-49): mp 143.3-144.9° C.

Provenance & Evidence