Synthesis
To 2,4,6-trichloropyridine (10.0 g, 55.6 mmol) and dimethylamine hydrochloride (4.5 g, 55.6 mmol) in N,N-dimethylformamide (DMF, 80 mL) was added triethylamine (Et3N, 8.0 g, 55.6 mmol). The reaction mixture was placed in a sealed tube, heated to 80 °C and maintained for 8 hours. After completion of the reaction, the mixture was diluted with water and extracted with ethyl acetate (EtOAc). The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to afford the target product 2,6-dichloro-N,N-dimethylpyridin-4-amine (12-TT, 4.0 g) as a white solid.1H-NMR (DMSO-d6, 400 MHz): δ=6.66 (s, 2H), 2.99 (s, 6H).
