N,N'-Dimethylethylenediamine → HCID 57540632, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(4-(trifluoromethoxy)phenylthio)pyrazin-2(1H)-one (100 mg, 0.347 mmol), 1-(4-bromo-2-methylphenoxy)-2-methylpropan-2-ol (90 mg, 0.347 mmol), N1,N2-dimethylethane-1,2-diamine (92 mg, 1.041 mmol), copper(I) iodide (19.82 mg, 0.104 mmol) and K3PO4 (221 mg, 1.041 mmol) in dioxane (1.0 mL) was stirred at 115° C. in a sealed tube for 2 hours. After removal of the precipitate by filtration, the filtrate was concentrated. The crude product was purified by silica gel chromatography employing a solvent gradient (hexane to 100% EtOAc) to elute 1-(4-(2-hydroxy-2-methylpropoxy)-3-methylphenyl)-3-(4-(trifluoromethoxy)phenylthio)-pyrazin-2(1H)-one (18.65 mg, 0.040 mmol, 11.52% yield) as off-white solid. 1H NMR (500 MHz, methanol-d3) δ ppm 7.62-7.68 (2H, m), 7.37 (2H, d, J=7.97 Hz), 7.21-7.28 (3H, m), 7.16 (1H, d, J=4.40 Hz), 7.02 (1H, d, J=8.25 Hz), 3.84 (2H, s), 2.31 (3H, s), 1.36 (6H, s).

Provenance & Evidence