443649-18-1

White to light yellow solid

General procedure for the synthesis of 5-aminopyridine-3-methanol from 5-aminopyridine-3-carboxylic acid methyl ester: 5-aminopyridine-3-carboxylic acid methyl ester (5.7 g, 30.2 mmol) was dissolved in tetrahydrofuran (THF, 150 mL) and lithium aluminum hydroxide (LiAlH4, 1 M THF solution, 133 mL, 133 mmol) was added slowly at 0 °C. The reaction mixture was stirred at room temperature for 21 hours. Upon completion of the reaction, the reaction mixture was quenched with dilute hydrochloric acid (HCl) and acidified to pH 3, followed by alkalization with solid sodium carbonate (Na2CO3) to pH 8. The solvent was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography using 20% methanol (MeOH)/dichloromethane (DCM) as eluent to afford the target product 5-aminopyridine-3-methanol (3.8 g, 100% yield), which was analyzed by liquid chromatography coupled with mass spectrometry (LCMS) showing a purity of 97% with a mass-to-charge ratio (m/z) of 125 [M+H]+ and the detector was an evaporative light scattering detector (ELS).

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