23794-15-2

1-(2-Chloro-4-pyridinyl)ethanone is used for the synthesis of pyrimidine derivatives as hSMG-1 inhibitors in the treatment of cancer.

Step 2: Synthesis of 1-(2-chloropyridin-4-yl)ethanone To a solution of 2-chloro-N-methoxy-N-methylisonicotinamide (10.0 g, 50 mmol) in anhydrous tetrahydrofuran (50 mL) was slowly added 3M methylmagnesium bromide solution in tetrahydrofuran (50 mL, 150 mmol) at 0 °C, keeping stirring. After addition, the reaction mixture was gradually warmed to room temperature and stirring was continued overnight. Upon completion of the reaction, the reaction was quenched with saturated aqueous ammonium chloride solution, followed by extraction of the organic phase with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to afford 1-(2-chloropyridin-4-yl)ethanone (7.5 g, 96% yield). Mass spectrometric analysis (ESI) showed m/z: 156.0 [M + H]+.

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