2-Methylaziridine → HCID 85999420, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-5-(chloromethyl)pyridine (352 mg, 2.17 mmole) in 4 mL of dry acetonitrile is 0.4 mL (4.34 mmol) of 2-methyl-aziridine followed by 300 mg (2.17 mmol) of potassium carbonate. The reaction is heated at 60° C. for 20 h. After cooling, the reaction mixture is quenched with 5 mL of water, extracted three-times with methylene chloride, and dried over sodium sulfate. Concentration of the solvent provided an oil which was purified by silica gel chromatography to provide 66 mg (17% yield) of 2-Chloro-5-(2-methyl-aziridin-1-ylmethyl)-pyridine. Diagnostic 1H NMR (400 MHz, CDCl3) 1.15 (d, 3H, J=5.4 Hz), 1.34 (d, 1H, J=6.6 Hz), 1.47–1.55 (m, 2H), 3.35 (abq, 2H, J=5.8 Hz), 7.25 (d, 1H, J=6.3 Hz), 7.65 (dd, 1H, J=8.3 and 2.5 hz), 8.27 (d, 1H, J=1.7 Hz); MS 183.2 (M+H).

Provenance & Evidence