N,N'-Dimethylethylenediamine → HCID 25169199, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(phenethylthio)pyrazin-2(1H)-one (25 mg, 0.108 mmol), which was prepared by the procedure described in Method 7 except for substitution of 2-phenethylthiol for 2-(4-chlorophenethanol), 1-(4-bromo-2-methylphenoxy)-2-methylpropan-2-ol (33.5 mg, 0.129 mmol), copper iodide (20.50 mg, 0.108 mmol), K3PO4 (70 mg, 0.323 mmol) and N,N′-dimethylethylenediamine (28.5 mg, 0.323 mmol) in dioxane (1.0 ml) was stirred at 115° C. for 2 hours. The reaction mixture, after cooling to RT, was filtered and the filtrate was concentrated. The crude product was purified by silica gel chromatography employing a solvent gradient (hexane to 100% ethyl acetate) to elute to yield 1-(4-(2-hydroxy-2-methylpropoxy)-3-methylphenyl)-3-(phenethylthio)-pyrazin-2(1H)-one (26.74 mg, 0.062 mmol, 57.5% yield) as off-white solid. MS (M+1=411). 1H NMR (500 MHz, methanol-d3) δ ppm 7.38 (1H, d, J=4.40 Hz), 7.25-7.32 (4H, m), 7.16-7.24 (4H, m), 7.00 (1H, d, J=8.25 Hz), 3.83 (1H, s), 3.24-3.39 (2H, m), 2.90-3.05 (2H, 2.29 (3H, s), 1.35 (6H, s).

Provenance & Evidence