Aluminium lithium hydride → 2-(5-Aminopyridin-2-yl)ethan-1-ol

To a solution of methyl 2-(5-aminopyridin-2-yl)acetate (0.250 g, 1.5 mmol) in THF (20 mL) at 0° C. was added lithium aluminum hydride (1.0 M, 3.75 mL, 3.75 mmol). The mixture was warmed to rt and stirred for 2 h. After this time, the reaction was quenched with water and NaOH (2 M), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography (silica, dichloromethane/methanol) to afford the title compound (0.046 g, 22%) as an orange oil. MW=138.17. 1H NMR (CDCl3, 500 MHz) δ 8.01-7.97 (m, 1H), 6.97-6.92 (m, 2H), 3.96 (t, J=5.5 Hz, 2H), 3.60 (s, 2H), 2.89 (t, J=5.5 Hz, 2H); APCI MS m/z 139 [M+H]+.

1. customAfter this time, the reaction was quenched with water and NaOH (2 M)
2. dry with materialdried over anhydrous sodium sulfate
3. filtrationfiltered
4. concentrationthe filtrate was concentrated
5. customThe residue was purified by column chromatography (silica, dichloromethane/methanol)

ORD record

ord-1337593b26244ba89263b207e5845577

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09221843B2