Water → 8-amino-7-chloro-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one

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Reaction Steps

To a stirred solution of 8-amino-7-chloro-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one (1.41 g, 7.6 mmol) in DMF (10 mL) at room temperature under argon was added 5-(chloromethyl)-2-(trifluoromethyl)pyridine (1.78 g, 9.1 mmol), followed by K2CO3 (2.1 g, 15.2 mmol). The resulting mixture was stirred at room temperature for 5 h. Analysis by HPLC/MS indicated that the reaction was complete. Water (50 mL) was added to the reaction mixture. The solid precipitate was collected by filtration and was washed with water (10 mL×3). After the resulting solid was dried under vacuum, the title compound (2.4 g) was obtained as an off-white solid. HPLC/MS: retention time 2.43 min, [M+H]30 =345. 1H NMR (CDCl3): δ 8.81 (s, 1H), 8.12 (s, 1H), 7.92 (d, J=7.0 Hz, 1H), 7.69 (d, J=7.0 Hz, 1H), 5.21 (s, 2H), 4.42 (s, 2H). N-alkylation, rather than O-alkylation, was demonstrated by the presence of a 13C NMR resonance at 46.9 ppm.

Provenance & Evidence