3-Methoxyphenol → HCID 9996740, compound

Participants

Reaction Steps

TMAD (0.060 g, 0.35 mmol) was dissolved in THF (1 mL) and DMF (0.5 mL) and the solution added dropwise to a mixture of 2-[3-(4-tert-butoxycarbonyl-1-piperazinyl)-pyrazinyloxy]ethanol (0.100 g, 0.310 mmol), triphenylphosphine (0.092 g, 0.35 mmol) and 3-methoxyphenol (0.124 g, 1.00 mmol) in THF (0.5 mL). The reaction mixture was stirred overnight at room temperature, concentrated, and put through a silica column using toluene/EtOAc (7:3) as eluent. Solvents were removed in vacuo and the N-t-BOC derivative of the title compound was treated with dichloromethane/TFA/H2O (50:45:5; 5 mL) for 15 min. The mixture was concentrated and the residue was 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 40 mg (34%) of the title compound as an oil. HRMS m/z calcd for C17H22N4O3 (M)+ 330.1692, found 330.1677.

Provenance & Evidence