905281-60-9

123367-27-1

60-34-4

905281-61-0

905281-60-9

To a 50 mL ethanol solution of (E)-3-(dimethylamino)-1-(pyridin-4-yl)prop-2-en-1-one (1.00 g) was added 0.32 mL of methylhydrazine, and the reaction mixture was heated to reflux and held for 1 hour. Upon completion of the reaction, the solvent was removed by rotary evaporation. The residue was partitioned between ethyl acetate and water. The aqueous layer was extracted with another portion of ethyl acetate. The organic phases were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated to give 0.62 g of crude product as a yellow oil. The crude product was purified by column chromatography using dichloromethane with methanol (10:1, v/v) as eluent to give 0.30 g (64% yield) of the target compound as a yellow oil.1H NMR (CDCl3) analysis showed the product to be a mixture of the desired compound with the by-product 4-(1-methyl-1H-pyrazol-3-yl)pyridine in a ratio of 3.8:1. LC/ MS analysis (positive ion ESI mode) showed two peaks with respective [M+H]+ molecular ion peak m/z of 160.2.