Water → 3-Cyclopentyl-4-methyl-2-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxy)-7-phenylpyrazolo[1,5-d][1,2,4]triazine

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Reaction Steps

To toluene-4-sulfonic acid 3-cyclopentyl-4-methyl-7-phenylpyrazolo[1,5-d][1,2,4]triazin-2-yl ester (Example 5, step a; 300 mg, 0.67 mmol) and (2-methyl-2H-[1,2,4]triazol-3-yl)methanol (90.4 mg, 1.2-molar eq; prepared as described in EP-A-170073) in DMF (10 ml) was added sodium hydride (29.5 mg of a 60% dispersion in mineral oil; 1.2 molar eq) and the mixture was stirred at room temperature for 1 h. Water (90 ml) was added then the solution was extracted with diethyl ether (4×50 ml). The combined ether layers were washed with brine (1×100 ml), dried (Na2SO4), the solvent was removed in vacuo and the residue was purified by flash chromatography on silica gel eluting with 0 to 50% ethyl acetate in dichloromethane. 3-Cyclopentyl-4-methyl-2-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxy)-7-phenylpyrazolo[1,5-d][1,2,4]triazine was isolated as a gum, which solidified upon trituration under diethyl ether (152 mg, mp=159° C.). 1H NMR (360 MHz, CDCl3) δ 1.66-1.96 (8H, m), 2.86 (3H, s), 3.44 (1H, m), 3.87 (3H, s), 5.54 (2H, s), 7.61-7.58 (3H, m), 7.90 (1H, s), 8.24-8.26 (2H, m); MS (ES+) m/e 389 [MH]+. Anal. Found C, 65.02; H, 5.97; N, 25.31%. C21H23N7O requires C, 64.76; H, 5.95; N, 25.18%.

Provenance & Evidence