Potassium tert-butoxide → HCID 90386249, compound

Participants

Reaction Steps

To a solution of (±)-2-(5-phenyl-4-((pyridin-2-ylmethyl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)cyclopropanecarbonitrile (550 mg, 1.50 mmol) in t-butanol (30 mL) was added KOtBu (842 mg, 7.51 mmol). The reaction mixture was heated to reflux at 90° C. for 12 h. t-Butanol was evaporated under reduced pressure and water (25 mL) was added to the reaction mixture. The aqueous layer was acidified with aqueous citric acid solution and extracted with DCM (3×50 mL). The combined organic extracts were washed with brine (25 mL), dried over sodium sulfate and concentrated. The residue was purified by preparative HPLC (Condition B-108 as described in general methods) to obtain (±)-2-(5-phenyl-4-((pyridin-2-ylmethyl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)cyclopropanecarboxamide (130 mg, 22.0%) which was resolved by chiral HPLC (Condition B-109 as described in general methods) to obtain enantiomer-1 (42 mg) and enantiomer-2 (46 mg).

Provenance & Evidence