1,4-Dioxane → Tert-butyl 7-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-(1-ethoxyvinyl)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-3-oxa-9-azabicyclo[3.3.1]nonane-9-carboxylate

Participants

Reaction Conditions

Reaction Steps

tert-butyl 7-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-bromo-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-3-oxa-9-azabicyclo[3.3.1]nonane-9-carboxylate (150 mg, 0.176 mmol) in dioxane (2 mL) was treated with Pd(PPh3)4 (20.3 mg, 0.0.176 mmol) and tributyl(1-ethoxyvinyl)tin (0.18 mL, 0.528 mmol) under argon and the mixture was heated at 100° C. for 16 h. Upon cooling, the mixture was filtered through a pad of 10% KF—SiO2 and the filtrate was evaporated off under reduced pressure to give a residue which was purified by column chromatography (SiO2, 0-40% hexane-EtOAc) to provide desired compound tort-butyl 7-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-(1-ethoxyvinyl)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-3-oxa-9-azabicyclo[3.3.1]nonane-9-carboxylate. HPLC-MS tR=3.65 min (UV254 nm). Mass calculated for formula C45H66N6O6Si2 842.4; observed MH+ (LCMS) 843.2 (m/z).

Provenance & Evidence