846036-96-2

General procedure for the synthesis of (4-amino-6-chloropyridin-3-yl)methanol from ethyl 4-amino-6-chloronicotinate: lithium aluminum hydride (LiAlH4, 1.9 g) was suspended in tetrahydrofuran (THF, 50 mL) and cooled at -78 °C. Subsequently, a solution of ethyl 4-amino-6-chloronicotinate (5.1 g, 25.4 mmol) in tetrahydrofuran (THF, 70 mL) was added slowly and dropwise. The reaction mixture was stirred continuously at -78 °C for 3 h and then gradually warmed up to room temperature. Upon completion of the reaction, a mixture of methanol (MeOH) and ethyl acetate (EtOAc) (1:1, v/v) was slowly added to quench the reaction and the solid was removed by filtration. The filtrate was concentrated and the resulting residue was purified by silica gel column chromatography (eluent ratio petroleum ether (PE):ethyl acetate (EtOAc) = 10:5:1) to give (4-amino-6-chloro-pyridin-3-yl)methanol (2.6 g, 65% yield) as a pale yellow solid.

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