Sodium hydride → 6-(2-Methyl-2h-tetrazol-5-ylmethoxy)-3,7-diphenyl-1,2,4-triazolo[4,3-b]pyridazine

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Reaction Steps

To the product from Example 73, Step a (0.15 g, 0.52 mmol) in anhydrous DMF (5 ml) was added sodium hydride (60% dispersion in oil, 31.2 mg, 0.780 mmol) and the mixture was stirred under nitrogen at room temperature for 45 min then at 80° C. for another 20 min. After allowing to cool, a solution of 5-chloromethyl-2-methyl-2H-tetrazole (Moderhack, D., Chem. Ber., 1975, 108, 887-896) (0.103 g, 0.780 mmol) in anhydrous DMF (4 ml) was added and the mixture was stirred at room temperature under nitrogen for 1.5 h, then at 80° C. for 17 h. The mixture was then partitioned between water (30 ml) and ethyl acetate (40 ml). The aqueous layer was further extracted with ethyl acetate (9×40 ml) and the combined organic extracts were dried (MgSO4), and evaporated in vacuo. The residue was recrystallised from EtOAc—CH2Cl2—MeOH to afford 0.1002 g (50%) of the title compound as a white solid: mp 228-233° C.; 1H NMR (360 MHz, CDCl3) δ 4.36 (3H, s), 5.79 (2H, s), 7.47-7.60 (8H, m), 8.07 (1H, s), 8.48 (2H, m); MS (ES+) m/e 385 [MH]+. Anal. Found C, 62.01; H, 4.13; N, 28.92. C20H16N8O. 0.17H2O requires C, 62.00; H, 4.25; N, 28.92%.

Provenance & Evidence