Toluene → 2-(2,6-Dichloro-4-pyridyl)-5,6-diethyl-5-methoxycarbonyl-3-propargyl-5,6-dihydropyrimidin-4-one

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Reaction Steps

To 3.15 g (78 mmol) of sodium hydride in 50 mL of dimethylformamide at 0° C. was added dropwise over 1.5 hr a solution of 26.9 g (75 mmol) of 2-(2,6-dichloro-4-pyridyl)-5,6-diethyl-5-methoxycarbonyl-5,6-dihydropyrimidin-4-one in 200 mL of dimethylformamide. When this addition was complete 12.5 mL (16.73 g, 112.5 mmol) of 80% propargyl brmide in toluene was added and the reaction stirred at room temperature overnight. Upon completion the reaction was quenched onto 600 mL of ice/water, extracted with ethyl acetate (3×400 mL), the organics were combined, washed with water (2×300 mL) and saturated sodium chloride (2×500 mL), dried over Na2SO4, filtered and evaporated to dryness in vacuo to give 29.23 g (73.8 mmol, 98%) of the desired product as a yellow solid.

Provenance & Evidence