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

Participants

Reaction Conditions

Reaction Steps

N1,N2-dimethylethane-1,2-diamine (356 mg, 4.04 mmol) was added to a stirred mixture of 1-(4-bromo-2-methoxyphenoxy)-2-methylpropan-2-ol Part 1B of Procedure 1 (222 mg, 0.807 mmol), 4-(4-chlorobenzylthio)pyrimidin-2(1H)-one Part A (170 mg, 0.67 mmol), copper(I) iodide (77 mg, 0.404 mmol) and potassium phosphate, tribasic (857 mg, 4.04 mmol) in dioxane (8 mL). The mixture was stirred at 105° C. for 7 h. The reaction mixture was diluted with methylene chloride, washed with saturated sodium bicarbonate, dried (MgSO4) and concentrated. The crude product was subjected to ISCO flash chromatography (silica gel/hexane-EtOAc 100:0 to 0:100 gradient, used LC/MS to identify fractions containing the desired product) to afford the title compound 4-(4-chlorobenzylthio)-1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)pyrimidin-2(1H)-one A-1 (22 mg, 0.048 mmol, 7% yield, eluted with 100% EtOAc) as a pale gummy solid.

Provenance & Evidence