Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1) → HCID 70216569, compound

Participants

Reaction Steps

To tert-butyl (7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-bromo-3-(6-fluoroquinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)methyl(1-(hydroxymethyl)cyclopropyl)carbamate (0.19 g, 0.23 mmol) in DCM (2.5 ml) was added protonsponge (70 mg, 0.33 mmol) followed by trimethyloxoniumtetrafluoroborate (48.2 mg, 0.33 mmol) at room temperature and the resulting mixture was stirred at room temperature for 16 h, at which time LC/MS confirmed full conversion of starting material to product. Reaction mixture was quenched with sat. NH4Cl and diluted with DCM (25 ml). Organics were separated and washed with brine (5 ml) and dried over MgSO4. Solvent was removed in vacuo and the residue was purified by column chromatography on silica gel. Elution with DCM/MeOH (0-50%) gave slightly impure desired tert-butyl (7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-bromo-3-(6-fluoroquinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)methyl(1-(methoxymethyl)cyclopropyl)carbamate (97 mg, 50%).

Provenance & Evidence