4-Aminopyridine → Methyl 3-oxo-3-[(pyridin-4-yl)amino]propanoate

Participants

Reaction Steps

A mixture of 3-chloro-3-oxopropanoate (1 mL, 9.32 mmol), pyridin-4-amine (0.88 g, 9.32 mmol), and Et3N (1.3 mL, 9.32 mmol) in DCM (18.6 mL) was stirred for 2 h at room temperature. The mixture was concentrated and the residue was purified by flash chromatography (eluent EtOAc/MeOH, 19/1) to produce methyl 3-oxo-3-(pyridin-4-ylamino)propanoate (507.7 mg). Part of this material (207 mg) was re dissolved in THF (1 mL); treated with LiOH×H2O (90 mg, 2.14 mmol) in H2O (1 mL) for 1 h at room temperature. The THF was removed under reduced pressure and the residue was lyophilized to afford the title compound 33 (containing 1 equivalent LiCl) (243.1 mg, 100% yield) as a white solid, which was used in the next step without further purification. MS (m/z): 181.0 (M+H).

Provenance & Evidence