Ethanol → 5-(4-ethylphenoxy)pyrimidin-4(3H)-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-(4-ethylphenoxy)-2-(mercapto)pyrimidine-4(3H)-one (2.49 g, 10.28 mmoles), ethanol (250 mL) and wet Raney Ni (50% slurry in water, active catalyst) (Aldrich) (10.9 g) was refluxed with stirring for 3 hours. The reaction was cooled to about 40° C. and filtered through a pad of Celite 545 (Fisher). The pad was washed with hot ethanol (2×75 mL), and the pad was placed in a beaker of water. The combined filtrates were spin evaporated in vacuo to a syrup. The syrup was dissolved in ethyl acetate and reevaporated to give a gray solid. The solid was dissolved in ethyl acetate (40 mL) and applied to a column (4.2×9.5.cm) of Silica Gel 60 (E.M. Science, 230-440 mesh) that was equilibrated with ethyl acetate. The column was eluted with ethyl acetate by flash chromatography, and twelve 100 mL fractions were collected. Fractions 4-10 were combined and spin evaporated in vacuo. The residual oil was dissolved in ethyl acetate and evaporated to give a mixture of light green and white crystals. The crystals were dissolved in dichloromethane and spin evaporated in vacuo to give 1.37 g (63% yield) of 5-(4-ethylphenoxy)pyrimidine-4(3H)-one. Recrystallization of a sample form ethyl acetate gave analytically pure 5-(4-ethylphenoxy)-2-(mercapto)pyrimidine-4(3H)-one as white needles, mp 144-146° C.

Provenance & Evidence