Ethyl orthoformate → ethyl [5-(1H-tetrazol-1-yl)pyrazin-2-yl]acetate

Participants

Reaction Conditions

Reaction Steps

A solution of the ethyl (5-aminopyrazin-2-yl)acetate (2.0 g, 11.0 mmol) and triethyl orthoformate (4.9 g, 33.1 mmol) in 60 mL of HOAc was added sodium azide (0.9 g, 13.8 mmol) and heated to 100° C. for 1 hour. The reaction was completed which was checked by TLC. The reaction mixture was cooled to r.t. The solvent was removed under vacuum. The residue was dissolved in EtOAc, washed with water, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatograph to afford the product ethyl [5-(1H-tetrazol-1-yl)pyrazin-2-yl]acetate. 1H-NMR (400 MHz, CDCl3) δ ppm 9.50 (s, 1H), 9.35 (s, 1H), 8.54 (s, 1H), 4.21 (q, J=7.2 Hz, 2H), 3.98 (s, 2H), 1.27 (t, J=7.2 Hz, 3H).

Provenance & Evidence