Sodium hydride → HCID 70215340, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate (311 mg, 1.44 mmol) and sodium hydride (60% in mineral oil, 58 mg, 1.44 mmol) in THF (2 ml) under argon at room temperature was added 5-chloro-3-(quinolin-3-yl)-N,N-bis((2(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (400 mg, 0.72 mmol). The mixture was heated at 100° C. for 30 min in microwave. Ethyl acetate (50 ml) was added and the mixture was washed with brine and water, dried over Na2SO4, and concentrated in vacuo. The crude product was dissolved in acetonitrile, followed by the addition of N-bromosuccinimide (193 mg, 1.08 mmol). The reaction mixture was stirred at room temperature for 2 h, concentrated in vacuo and purified via silica gel chromatography (10% to 50% ethyl acetate in hexanes gradient) to yield the title compound (0.56 g, 95% yield). LC-MS: 813 [M+H].

Provenance & Evidence