63155-11-3

1722-12-9

105-53-3

63155-11-3

To a solution of diethyl malonate (6.65 mL, 43.65 mmol) in anhydrous DMF (30 mL) at -78 °C was slowly added sodium hydride (1.76 g, 52.38 mmol, 60% mineral oil dispersion). The reaction mixture was stirred at -78 °C for 10 min and then gradually warmed to room temperature, followed by dropwise addition of anhydrous DMF (3 mL) solution of 2-chloropyrimidine (1.0 g, 8.73 mmol). The reaction system was heated to 80 °C and maintained for 72 h. The reaction was then warmed up to 120 °C and continued for 18 h. The reaction was then completed. Upon completion of the reaction, the mixture was cooled to room temperature, the reaction was quenched with 1N HCl solution, neutralized with saturated aqueous NaHCO3 solution and extracted with ethyl acetate (3 x 30 mL). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: 0-100% ethyl acetate in hexane solution with gradient elution) to afford ethyl 2-pyrimidineacetate as a yellow-orange oil (1.34 g, 92% yield). Mass spectrometry (MS) showed the molecular ion peak m/z 167 (MH+).