Reaction Steps
To a solution of 8 -phenylpyrano [3,4-b]pyridin-5-one (102 mg, 0.46 mmoles) in 2 ml DMF was added 4-picolylamine (0.055 ml, 0.55 mmoles) under nitrogen. The reaction mixture was heated overnight to 80° C., cooled and then concentrated under vacuum to give 0,335 g crude product which was chromatographed eluting with 1:1 ethyl acetate/hexanes to give 69 mg (48% yield) of the desired 6-(4-pyridylmethyl)-8-phenyl-1,6-naphthyridin-5-one as a white solid. Characteristic analytical data are as follows: mp 199.5°-200.5° C.; 1H NMR (CDCl3,300 MHz) δ5.30 (s, 2H), 7.26 (d, 2H, J=6), 7.34-7.59 (m, 7H), 8.6 (d, 2H, J=6), 8.78 (dd, 1H, J=8.04, 2.00), 8.99 (dd, 1H, J=4.39, 1.83); 13C NMR (75 MHz, CDCl3) δ161.90, 154.52, 152.09, 150.08, 145.44, 136.72, 134.77, 133.67, 129.96, 128.40, 127.92, 122.44, 122.16, 121.90, 121.81, 51.18; IR (KBr) vmax 3445, 1655, 1624, 1599, 1437, 1421, 1373, 1169, 1099, 993,922, 868, 794, 763, 727, 707, 677, 607, 598, 522 cm-1 ; mass spectrum (EI), m/e 313. Anal. (C20H15N3O 3/4 H2O) Calcd.: C, 73.49; H, 5.09; N, 12.86. Found: C, 73.73; H, 4.99; N, 12.36.
