4-Chlorobenzyl mercaptan → 4-(4-chlorobenzylthio)-1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)pyrimidin-2(1H)-one

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Reaction Conditions

Reaction Steps

A mixture of 1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)-4-(methylthio)pyrimidin-2(1H)-one (90 mg, 0.268 mmol) and (4-chlorophenyl)methanethiol (707 μl, 5.35 mmol) was heated to 145° C. (neat) for 30 min. The mixture was diluted with methylene chloride, washed with water, dried (Na2SO4) and concentrated. The crude product was subjected to ISCO flash chromatography (silica gel/hexanes:ethyl acetate 100:0 to 0:100 gradient) to afford the title compound 4-(4-chlorobenzylthio)-1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)pyrimidin-2(1H)-one A-1 (83.5 mg, 0.187 mmol, 69.8% yield) as a yellow solid. LC/MS 447 (M+H)+, tR 0.93 (method 5); 1H NMR (400 MHz, chloroform-D) δ 7.33-7.44 (3H, m), 7.24-7.31 (2H, m), 6.91-6.99 (2H, m), 6.86 (1H, dd, J=8.53, 2.51 Hz), 6.24 (1H, d, J=7.03 Hz), 4.48 (2H, s), 3.86 (3H, s), 3.85 (2H, s), 1.35 (6H, s).

Provenance & Evidence