Cesium carbonate → 6-(2-Methyl-2h-[1,2,4]triazol-3-ylmethoxy)-1-phenyl-1h-pyrazolo[3,4-b]pyridin-4-ylamine

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Reaction Conditions

Reaction Steps

To a solution of 4-amino-1,7-dihydro-1-phenylpyrazolo[3,4-b]pyridin-6-one (0.30 g, 1.33 mmol) in DMF (8 ml) under nitrogen was added cesium carbonate (0.95 g, 2.92 mmol) followed by 3-chloromethyl-2-methyl-2H-[1,2,4]triazole hydrochloride (0.27 g, 1.61 mmol). The resulting suspension was heated at 60° C. for 17 h. The mixture was partitioned between saturated aqueous ammonium chloride solution and ethyl acetate. The layers were separated and the aqueous phase extracted a second time with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo to give the title compound as a white solid (0.41 g, 96%), m.p. 164-166° C. δH (400 MHz; CDCl3) 3.91 (3H, s), 4.70 (2H, br s), 5.58 (2H, s), 5.89 (1H, s), 7.28-7.31 (1H, m), 7.48-7.52 (2H, m), 7.88 (1H, s), 7.98 (1H, s), 8.15-8.18 (2H, m); m/z (ES+) 322 (M+H+).

Provenance & Evidence