Stannane, tributyl(1-ethoxyethenyl)- → HCID 66733551, compound

Participants

Reaction Conditions

Reaction Steps

A degassed mixture of 6-bromo-5-morpholino-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (141 mg, 0.20 mmoL), tributyl(1-ethoxyvinyl)tin (112 mg, 0.31 mmoL), Pd(PPh3)4 (24 mg, 0.02 mmoL) in Dioxane (4 mL) was heated at 100° C. for 2 days. The mixture was cooled to room temperature and filtered through short plug of 10% KF/SiO2. The crude Stille coupling product obtained after concentrating the filtrate was then treated with 3 mL of 1:1 mixture of TFA and H2O at room temperature for 30 min. Concentration and purification by prep-LC afforded 1-(7-amino-5-morpholino-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-6-yl)ethanone. LCMS tR=3.32 Min. Mass calculated for, M+ 388.1, observed LC/MS m/z 389.1 (M+H).

Provenance & Evidence