N,N'-Dimethylethylenediamine → 1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)-4-(methylthio)pyrimidin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

After addition of N,N′-Dimethylethane-1,2-diamine (1.6 g, 18.15 mmol) to a stirred mixture of 4-(methylthio)pyrimidin-2(1H)-one Part A (430 mg, 3.02 mmol), 1-(4-bromo-2-methoxyphenoxy)-2-methylpropan-2-ol Part B (1.0 g, 3.63 mmol), copper(I)iodide (346 mg, 1.82 mmol) and potassium phosphate, tribasic (3.85 g, 18.15 mmol) in 3:1 dioxane-DMF (80 mL), the mixture was stirred at 105° C. for 7 h. The reaction mixture was diluted with CH2Cl2, washed with saturated NaHCO3, dried (MgSO4) and concentrated. The crude product was subjected to flash chromatography (silica gel/hexane-EtOAc 100:0 to 0:100 gradient) to afford 1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)-4-(methylthio)pyrimidin-2(1H)-one 1C (0.375 g, 37% yield). 1H NMR (400 MHz, chloroform-D) δ 7.37 (1H, d, J=7.03 Hz), 6.95 (1H, d, J=8.53 Hz), 6.92 (1H, d, J=2.51 Hz), 6.85 (1H, dd, J=8.53, 2.51 Hz), 6.28 (1H, d, J=7.03 Hz), 3.85 (3H, s), 3.84 (2H, s), 2.61 (3H, s), 2.59 (1H, s), 1.35 (6H, s).

Provenance & Evidence