53342-27-1

14080-23-0

75-16-1

53342-27-1

1-(Pyrimidin-2-yl)vinyl ketone was synthesized as follows: a solution was prepared by dissolving pyrimidine-2-carbonitrile (75 g, 713.62 mmol) in THF (750 mL, 10 vol). The solution was slowly added dropwise to a THF solution of methylmagnesium bromide (750 mL THF containing 357 mL of 3.0 M diethyl ether solution, 1070.44 mmol) at -5 °C. The reaction mixture was stirred at 0 °C overnight. Subsequently, the reaction solution was slowly added to a rapidly stirred mixture of saturated ammonium chloride solution (750 mL) and 4 M HCl (450 mL) at 5 °C and the pH was adjusted to 1 with 2 M HCl (5 mL).The mixture was warmed to 20 °C with continuous stirring for 40 min, then cooled to 0 °C. The pH was adjusted to 6.5-7 with saturated K2CO3 solution (37.5 mL) and the phase separation was performed after warming to 10 °C. The aqueous phase was extracted with ethyl acetate (5 x 750 mL). The aqueous phase was saturated by the addition of sodium chloride and then extracted once more with ethyl acetate (750 mL). The pH of the aqueous phase was adjusted to 7-8 (using saturated K2CO3 solution) and further extracted with ethyl acetate (3 x 750 mL). All organic phases were combined, washed with saturated brine (750 mL), dried over MgSO4, filtered and concentrated under reduced pressure to give 78.9 g brown solid. The crude product was purified by rapid chromatography on silica gel using EtOAc as eluent. The pure grades were collected and evaporated to dryness to give 1-(pyrimidin-2-yl)ethanone (65.0 g, 74.6% yield) as a yellow crystalline solid.1H NMR (400.132 MHz, DMSO) δ 2.67 (3H, s), 7.72 (1H, t), 9.02 (2H, d); m/z (M+H)+, 123.