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3-Chloropyrazine-2-carboxylic acid (2.97 g, 18.73 mmol, 1 eq.) was dissolved in tetrahydrofuran (75 mL). The solution was stirred in an ice bath and triethylamine (5.2 mL, 37.5 mmol, 2 eq.) was added followed by addition of methyl chloroformate (1.74 mL, 22.5 mmol, 1.2 eq.) dropwise. After 30 m, the reaction was filtered and the solid rinsed with more tetrahydrofuran (10 mL). The tetrahydyofuran solution was stirred in an ice bath and a suspension of sodium borohydride (1.4 g, 37.5 mmol, 2 eq.) in water (3 mL) was added. After 1 h, a saturated aqueous ammonium chloride solution (100 mL) was added to the reaction and the mixture was extracted with ethyl acetate (2 x 100 mL). The combined organic phases were washed with a saturated aqueous sodium chloride solution (25 mL) and dried over sodium sulfate. After filtration and evaporation, the residue was purified by silica gel chromatography (5 - 70percent ethyl acetate/hexanes) to give (3-chloropyrazin-2-yl)methanol (0.84 g, 31percent) as a faintly colored oil.
22%
102901 To a solution of <strong>[27398-39-6]3-chloropyrazine-2-carboxylic acid</strong> (2.0 g, 12.70 mmol, 1.0 eq.) andTEA (3.50 mL, 25.40 mmol, 2.0 eq.) in THF (50 mL) was added methyl chloroformate (1.2 mL,15.20 mmol, 1.2 eq.) atO °C. The mixture was stirred at 0°C for 10 mm and filtered. To thisfiltrate was added a suspension of NaBH4 (0.97 g, 25.40 mmol, 2 eq.) in water (1.0 mL) at 0 °C. The mixture was stirred at 0 °C for 1 h, quenched with NH4C1 (aq) solution, and extracted with EtOAc twice. The combined organic layers were dried over Na2SO4, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give (3-chloropyrazin-2- yl)methanol (400 mg, 22percent) as a white solid. 1H NMR (400 MHz, MeOD) 8.58 (d,J 2.5 Hz,1H), 8.38 (d,J= 2.5 Hz, 1H), 4.84 (s, 2H). LRMS (M+H+) m/z 145.1.
With sodium tetrahydroborate; In methanol; at 20℃; for 1h;
To a solution of <strong>[121246-96-6]3-chloropyrazine-2-carbaldehyde</strong> (700mg, 4.91 mmol) in methanol (10ml) was dropwise NaBH4 (223mg, 5.89mmol). The reaction mixture was stirred at room temperature for 1 hr, and the reaction was terminated with a saturated aqueous ammonium solution, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated in a vacuum.
Step 1 To a solution of <strong>[27398-39-6]3-chloropyrazine-2-carboxylic acid</strong> (2.0 g, 12.70 mmol, 1.0 eq.) and TEA (3.50 mL, 25.40 mmol, 2.0 eq.) in THF (50 mL) was added methyl chloroformate (1.2 mL, 15.20 mmol, 1.2 eq.) at 0° C. The mixture was stirred at 0° C. for 10 min and filtered. To this filtrate was added a suspension of NaBH4 (0.97 g, 25.40 mmol, 2 eq.) in water (1.0 mL) at 0° C. The mixture was stirred at 0° C. for 1 h, quenched with NH4Cl(aq) solution, and extracted with EtOAc twice. The combined organic layers were dried over Na2SO4, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give (3-chloropyrazin-2-yl)methanol (400 mg, 22percent) as a white solid. 1H NMR (400 MHz, MeOD) delta 8.58 (d, J=2.5 Hz, 1H), 8.38 (d, J=2.5 Hz, 1H), 4.84 (s, 2H). LRMS (M+H+) m/z 145.1.
With vanadium nitrate; In acetonitrile; at 40℃; for 10h;Green chemistry;
1.44 g of 3-chloro-2-pyrazine methanol, 2 mol% of vanadium nitrate (relative to the substrate 3-chloro-2-pyrazine methanol),Add to the 50mL reaction tube, Add 5mL of acetonitrile,Fill the air ball, close the reaction tube, and raise the temperature to 40 C with stirring.And kept for 10 h, until the reaction is over, and cooled to room temperature.Sampling was analyzed using gas chromatography.The conversion rate of 3-chloro-2-pyrazine methanol is 96.1%.The selectivity of 3-chloro-2-pyrazinecarboxaldehyde is greater than 99%.
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