Tetrahydrofuran → HCID 9927823, compound

Participants

Reaction Steps

A mixture of 1-ethyl-N-[(4-carboxycyclohexyl)methyl]-1H-pyrazolo[3,4-b]quinolin-4-amine (5.0 g), THF (100 ml) and lithium aluminum hydride (3.0 g) is refluxed overnight. Additional lithium aluminum hydride (1.0 g) is added, and the mixture is heated at reflux for another hour. The reaction mixture is cooled, water (4 ml), then 10% NaOH (4 ml) and finally water (12 ml) are added, and the mixture is heated to reflux and then filtered. The collected solids are heated at reflux in TBF for 10 minutes, then filtered again. The filtrates are combined, dried over MgSO4 and then evaporated. The residue is purified by column chromatography on silica gel eluting with ethyl acetate and then is crystallized from hexanes/ethyl acetate. The product is dissolved in methanol, treated with methanesulfonic acid and then the methanol is evaporated. The residue is crystallized from 2-propanol and then recrystallized from 2-propanol to afford 1-ethyl-N-[(4-hydroxymethylcyclohexyl)methyl]-1H-pyrazolo[3,4-b]quinolin-4-amine.CH3SO3H, as a white solid, m.p. 188°-190° C.

Provenance & Evidence