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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).
ethyl 1-(2-fluorobenzyl)-5-methyl-1H-1,2,4-triazole-3-carboxylate[ No CAS ]
C13H14FN3O2[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
58%; 23%
A solution of ethyl 3 -methyl- 1H- 1 ,2,4-triazole-5-carboxylate in anhydrous DMF was treated with sodium hydride (60 wtpercent in mineral oil, 1.2 equiv.) and stirred for 10 min. 2- Fluorobenzyl bromide (1.2 equiv.) was added. After 16 hours, water was added and the aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with water and brine, dried over sodium sulfate, filtered, and the solvent was removed in vacuo. Purification by silica gel chromatography (10-50percent ethyl acetate in hexanes gradient) yielded ethyl l-(2-fluorobenzyl)-5-methyl-lH-l,2,4-triazole-3-carboxylate (58percent) and ethyl 1 -(2-fluorobenzyl)-3-methyl- 1H- 1 ,2,4-triazole-5-carboxylate (23percent)
5-methyl-1H-1,2,4-triazole-3-carboxylic acid trifluoroacetate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
460 mg
A mixture of <strong>[40253-47-2]ethyl 5-methyl-1H-1,2,4-triazole-3-carboxylate</strong> (1.0 g, 6.45 mmol) and sodium hydroxide (1.702 mL, 32.2 mmol) in tetrahydrofuran (30 mL) was stirred at ambient temperature for 16 hours. Volatiles were removed, and the residue was acidified with 1 N HCl solution. Water was removed under high vacuum, and the crude residue was purified by HPLC (0~70% acetonitrile in 0.1% trifluoroacetic acid/water on Phenomenex C1810 mum (250 mm × 50 mm) column at a flowrate of 50 mL/minute) to give 460 mg of the title compound as a white solid.
460 mg
A mixture of ethyl 5-methyl-lH-l ,2,4-triazole-3-carboxylate (1.0 g, 6.45 mmol) and sodium hydroxide (1.702 mL, 32.2 mmol) in tetrahydrofuran (30 mL) was stirred at ambient temperature for 16 hours. Volatiles were removed, and the residue was acidified with 1 N HQ solution. Water was removed under high vacuum, and the crude residue was purified by HPLC (0-70% acetonitrile in 0.1 % trifluoroacetic acid/water on Phenomenex C18 10 mupiiota (250 mm x 50 mm) column at a flowrate of 50 mL/minute) to give 460 mg of the title compound as a white solid.
(5-methyl-1H-1,2,4-triazol-3-yl)methanol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With lithium aluminium tetrahydride; at 0 - 30℃; for 1h;Inert atmosphere;
To a mixture of ethyl 5-methyl-1 H-1 ,2,4-triazole-3-carboxylate (200 mg, 1 .29 mmol) in THF (5 mL) was added LiAIH4(245 mg, 6.45 mmol) at 0C under N2. The mixture was stirred at 30C for 1 hour. The mixture was filtrated and washed with methanol, concentrated in vacuo to give(5-methyl-1 H-1 ,2,4-triazol-3-yl)methanol (350 mg).
350 mg
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 30℃; for 1h;Inert atmosphere;
To a mixture of <strong>[40253-47-2]ethyl 5-methyl-1H-1,2,4-triazole-3-carboxylate</strong> (200 mg, 1.29 mmol) in THE (5 mL) was added LiAIH4 (245 mg, 6.45 mmol) at 0C under N2. The mixture was stirred at 30C for 1 hour. The mixture was filtrated and washed with methanol, concentrated in vacuo to give(5-methyl-1H-1,2,4-triazol-3-yl)methanol (350 mg).
350 mg
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 30℃; for 1h;Inert atmosphere;
To a mixture of 285 <strong>[40253-47-2]ethyl 5-methyl-1H-1,2,4-triazole-3-carboxylate</strong> (200 mg, 1.29 mmol) in 166 THF (5 mL) was added 192 LiAlH4 (245 mg, 6.45 mmol) at 0 C. under N2. The mixture was stirred at 30 C. for 1 hour. The mixture was filtrated and washed with methanol, concentrated in vacuo to 286 give(5-methyl-1H-1,2,4-triazol-3-yl)methanol (350 mg).
350 mg
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 30℃; for 1h;Inert atmosphere;
To a mixture of ethyl 5-methyl-lH-l,2,4-triazole-3-carboxylate (200 mg, 1.29 mmol) in THF (5 mL) was added LiAIH4 (245 mg, 6.45 mmol) at 0C under N2. The mixture was stirred at 30C for 1 hour. The mixture was filtrated and washed with methanol, concentrated in vacuo to give(5-methyl-lH- l,2,4-triazol-3-yl)methanol (350 mg).
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