[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:9][CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[N:6][CH:7]=1.[H-].[Na+].[C:17](Cl)#[C:18][CH2:19][CH2:20][CH3:21].O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:9][CH2:10][C:11](=[O:14])[N:12]([CH2:17][C:18]#[C:19][CH2:20][CH3:21])[N:13]=2)=[N:6][CH:7]=1
To a 100 mL 3 neck flask equipped with magnetic stirrer, addition funnel, and nitrogen inlet was charged 200 milligrams (mg) of 6-(5-chloropyridin-2-yl)-4,5-dihydropyridazin-3(2H)-one (0.95 mmol), 3.8 mg of 60% sodium hydride (oil dispersion) (0.95 mmol), and 20 mL of dry DMF. The reaction mixture was stirred for about 30 minutes at ambient temperature followed by the dropwise addition of 0.1 ml of pentynyl chloride (0.95 mmol) in about 5 mL of dry DMF. The reaction was stirred overnight at ambient temperature, and checked by TLC and GC the next morning. No starting material remained, and one new product was formed. The reaction was poured into about 100 mL of water, and extracted with 3×50 mL of ethyl acetate. The combined ether extract was washed with 100 mL of water, 100 mL of saturated aqueous sodium chloride solution, dried, and stripped to afford 240 mg of a tan solid 92% isolated yield. The NMR data is a 1 follows: 300 MHz 1H NMR (CDCl3, TMS=0 ppm) 1.15 (t, 3H); 2.20 (m, 2H); 2.60 (t, 2H); 3.25 (t, 2H); 4.70 (s, 2H); 7.75 (d, 1H); 8.15 (d, 1H); 8.50 (s, 1H).
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