Reaction Steps
To a solution of 5-(4-methoxybenzyl)-7-(methylthio)-1,3,4,5-tetrahydro-1,2,5,6,8-pentaazaacenaphthylene (4.32 g, 13.22 mmol) in DMF (160 mL) was added Cs2CO3 (21.48 g, 66.11 mmol), BnBr (1.88 mL, 15.86 mmol) and NaI (0.5 g). The mixture was stirred at room temperature for 16 h. Ethyl acetate (250 mL) and water (150 mL) was added. The EtOAc layer was separated, washed with aqueous NaCl (3×150 mL), dried over Na2SO4, filtered and concentrated. The obtained residue was purified by flash silica gel chromatography (eluent: 50% then 60% EtOAc in hexane). Compound 129, 1-benzyl-5-(4-methoxybenzyl)-7-(methylthio)-1,3,4,5-tetrahydro-1,2,5,6,8-pentaazaacenaphthylene was obtained as a pale yellow solid (2.15 g, 39%). M.p. 168-170° C.; 1H NMR (CDCl3, 400 MHz) δ 7.31 (m, 5H), 7.25 (d, J=8.4 Hz, 2H), 6.85 (d, J=8.4 Hz, 2H), 5.42 (s, 2H), 4.76 (s, 2H), 3.79 (s, 3H), 3.52 (t, J=6.4 Hz, 2H), 3.02 (t, J=6.4 Hz, 2H), 2.62 (s, 3H). LC-Mass (m/e): 418.57 (M+1) and compound 129a, 1-benzyl-6-(4-methoxybenzyl)-4-(methylthio)-1,6,7,8-tetrahydro-1,2,3,5,6-pentaazaacenaphthylene was obtained as a pale yellow solid (2.35 g, 42%). M.p.>50° C.; 1H NMR (CDCl3, 400 MHz) δ 7.29 (m, 5H), 7.22 (d, J=8.8 Hz, 2H), 6.83 (d, J=8.8 Hz, 2H), 5.35 (s, 2H), 4.71 (s, 2H), 3.78 (s, 3H), 3.47 (t, J=6.0 Hz, 2H), 2.81 (t, J=6.0 Hz, 2H), 2.61 (s, 3H). LC-Mass (m/e): 418.57 (M+1).
