(S)-4-phenyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one → HCID 178519138, compound

Participants

Reaction Steps

To the solid (S)-4-phenyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one (0.80 g, 1.4 mmol) was added TFA (20 mL) and the reaction stirred at room temperature for 3 hours. The reaction was concentrated and the residue slurried in methanol/acetonitrile (20 mL 1:1) and water (20 mL) added and the reaction stirred at ambient temperature for 1 hour. The organic solvents were removed in vacuo and the water layer basified to about pH 7 using a solution of saturated NaHCO3. The aqueous layer was then stirred for 5 minutes. The solids were filtered and dried in vacuo. The solids were then taken up in water and stirred for 2 hours. The solids were filtered and dried in vacuo. The solids were next slurried in methanol while nitrogen was bubbled through the solution for 2 hours. The slurry was concentrated to about 20 mL, and the solids filtered and dried in vacuo to give (S)-3-(3-(4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-phenyloxazolidin-2-one (0.19 g, 0.45 mmol, 31% yield). LCMS (APCI+) m/z 424 [M+H]+.

Provenance & Evidence