Triphenylphosphine → HCID 10473299, compound

Participants

Reaction Steps

TMAD (0.207 g, 1.20 mmol) was added to a solution of 2-[3-(4-tert-butoxycarbonyl-1-piperazinyl)-pyrazinyloxy]ethanol (0.324 g, 1.00 mmol), triphenylphosphine (0.315 g, 1.20 mmol) and 2,3,4-trifluorophenol (0.296 g, 2.00 mmol) in THF (1 mL) at room temperature. After being stirred for 2 h, the mixture was concentrated in vacuo and put through a silica column using toluene/EtOAc (7:3) as eluent. Solvents were removed in vacuo and the resulting N-t-BOC derivative was treated with dichloromethane/TFA/H2O (50:45:5; 5 mL) for 15 min with stirring. The mixture was concentrated and the residue purified by chromatography on silica gel using EtOAc/HOAc/MeOH/H2O (20:3:3:2) as eluent. The product-containing fractions were concentrated, washed between dichloromethane/5% aqueous NaOH, and put through a silica column using dichloromethane/MeOH (8:2) as eluent to give 62 mg (17%) of the title compound. HRMS m/z calcd for C16H17F3N4O2 (M)+ 354.1304, found 354.1321.

Provenance & Evidence