Trifluoroacetic acid → Ammonium Hydroxide

Participants

Reaction Conditions

Reaction Steps

A solution of (5-cyanomethyl-pyrazin-2-yl)-carbamic acid tert-butyl ester (807.6 mg, 3.447 mol) in methylene chloride (4.3 mL) was treated with trifluoroacetic acid (2.7 mL, 34.470 mmol). The reaction mixture was stirred at 25° C. for 2 h and then concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 1/9 methanol/methylene chloride with 0.1% ammonium hydroxide) afforded impure (5-amino-pyrazin-2-yl)-acetonitrile. Re-purification by Biotage chromatography (FLASH 40M, Silica, 99/1 ethyl acetate/methanol) afforded pure (5-amino-pyrazin-2-yl)-acetonitrile (281.4 mg, 60.8%) as an orange solid: mp 132–134° C.; EI-HRMS m/e calcd for C6H6N4 (M+) 134.0592, found 134.0593.

Provenance & Evidence