Dimethylformamide → HCID 57907656, compound

Participants

Reaction Steps

To a 20 mL 1 neck flask equipped with magnetic stirrer, and nitrogen inlet was charged 30 milligrams (mg) of 6-(5-bromopyrimidin-2-yl)pyridazin-3(2H)-one (0.12 mmol), 33 mg of potassium carbonate (0.24 mmol), and 5 mL of dry DMF. The reaction mixture was stirred for about 30 minutes at ambient temperature followed by the addition of 100 mg of dec-2-ynyl methanesulfonate (0.43 mmol) in one portion. The reaction was stirred overnight at ambient temperature. The reaction was poured into about 10 mL of water, and extracted with 3×10 mL of ethyl acetate. The combined organic extract was washed with 10 mL of water, 10 mL of saturated aqueous sodium chloride solution, dried, and stripped to the crude product which was purified by silica gel column chromatography (20% ethyl acetate/80% hexanes). The pure fractions were combined and concentrated under vacuum on a rotary evaporator to afford 6 g of a white solid consistent with the title compound upon analysis by NMR. The NMR data is as follows: 300 MHz 1H NMR (CDCl3, TMS=0 ppm) 0.85 (m 3H); 1.25 (m, 6H); 1.60-1.65 (m, 4H); 2.15 (m, 2H); 5.05 (s, 2H); 7.05 (d, 1H); 8.35 (d, 1H); 9.00 (s, 2H).

Provenance & Evidence