89283-32-9

27398-39-6

89283-32-9

General procedure for the synthesis of 3-chloropyrazine-2-methanol from 2-chloropyrazine-3-carboxylic acid: 3-chloropyrazine-2-carboxylic acid (2.97 g, 18.73 mmol, 1 equiv) was dissolved in tetrahydrofuran (75 mL). The solution was stirred under ice bath conditions and the latter was added dropwise by adding triethylamine (5.2 mL, 37.5 mmol, 2 equiv.) and methyl chloroformate (1.74 mL, 22.5 mmol, 1.2 equiv.) sequentially. After 30 min of reaction, the reaction mixture was filtered and the solid was washed with additional tetrahydrofuran (10 mL). The resulting tetrahydrofuran solution was placed in an ice bath with stirring and a suspension of sodium borohydride (1.4 g, 37.5 mmol, 2 equiv) in water (3 mL) was slowly added. After 1 hour of reaction, saturated aqueous ammonium chloride solution (100 mL) was added to the reaction mixture, followed by extraction with ethyl acetate (2 x 100 mL). The organic phases were combined, washed with saturated aqueous sodium chloride solution (25 mL) and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated and the residue was purified by silica gel column chromatography (eluent: 5-70% ethyl acetate/hexane) to afford the target product (3-chloropyrazin-2-yl)methanol (0.84 g, 31% yield) as a light-colored oil.