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With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;
To a solution of ethyl 5-methyl-lH-l ,2,4-triazole-3-carboxylate (50 mg, 0.28 mmol) and 2-chloro-4-(chloromethyl)pyridine (50 mg, 0.31 mmol) in DMF (2 mL), K2CO3 (116 mg, 0.84mmol) was added. The mixture was stirred at RT overnight, and was then diluted with H20 (20 mL), extracted with EtOAc (3 x 20 mL), 4: 1 CHCl3: PrOH (3 x 20 mL), dried with MgS04 and concentrated under reduced pressure. The crude product was purified on a Biotage pre-packed silica gel column (EtOAc:Hexane 12percent to 100percent EtOAc) to afford ethyl l-((2- chloropyridin-4-yl)methyl)-5-methyl-lH-l ,2,4-triazole-3-carboxylate (29 mg, 40percent) as a white solid. MS(ES+) Ci2H13ClN402 requires: 280 found: 281 [M+H]+.
With ammonia; In methanol; at 50℃; for 24h;Sealed tube;
Ethyl 5-methyl- 1H- 1,2,4- triazole-3-carboxylate (3.0 g, 19.3 mmol) is placed in a sealed tube that is then charged with a solution of 7N N in MeOH (40 mL). The reaction is stirred at 50°C for 24 h. The solvent was then removed under reduced pressure and the crude material was used directly for the next step without further purification. MS(ES+) C4H6N40 requires: 126 found: 127 [M+H]+.
With potassium carbonate; In tetrahydrofuran; at 50℃; for 18h;
To a solution of ethyl 5-methyl-lH-l,2,4-triazole-3-carboxylate (1.0 g, 6.44 mmol) and l-bromo-3-(bromomethyl)benzene (1.77 g, 7.08 mmol) in THF (32 mL), K2CO3 (1.78 g, 12.88 mmol) was added. The mixture was stirred at 50°C for 18 h, and then the reaction was filtered under vacuum. The solvent was removed under reduced pressure and the crude product was purified on a Biotage pre-packed silica gel column (EtOAc:Hexane 12percent to 100percent EtOAc) to afford ethyl l-(3- bromobenzyl)-5-methyl-lH-l,2,4-triazole-3-carboxylate (1.25 g, 60percent) as a viscous oil. MS(ES+) Ci3H14BrN302 requires: 323, 325 found: 324, 326 [M+H]+(l :l).
60%
With potassium carbonate; In tetrahydrofuran; at 50℃; for 18h;
To a solution of ethyl 5-methyl-lH-l,2,4-triazole-3-carboxylate (1.0 g, 6.44 mmol) and l-bromo-3-(bromomethyl)benzene (1.77 g, 7.08 mmol) in THF (32 mL), K2CO3 (1.78 g, 12.88 mmol) was added. The mixture was stirred at 50°C for 18 h then filtered. The filtrate was concentrated under reduced pressure and the crude product was purified on a Biotage pre-packed silica gel column with a gradient of 12percent to 100percent EtOAc:Hexanes to afford ethyl l-(3-bromobenzyl)-5-methyl-lH- l,2,4-triazole-3-carboxylate (1.25 g, 60percent) as a viscous oil. MS(ES+) Ci3H14BrN302 requires: 323, 325 found: 324, 326 [M+H]+(l :l).
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