Ethyl Acetate → HCID 11217334, compound

Participants

Reaction Steps

To a solution of 3-aminopyridine (1.3 g, 13.4 mmol) in HOAc (20 mL) was added sodium azide (1.3 g, 20.1 mmol) and trimethyl orthoformate (2.36 mL, 21.6 mmol) and the resultant slurry was stirred at room temperature overnight and subsequently refluxed for 6 h. The reaction was cooled to room temperature and stopped by pouring into 50 mL of ice water. EtOAc (50 mL) was added, collected and subsequently washed with aqueous sodium hydroxide (1 N). The organic layer was collected, dried (MgSO4) and concentrated in vacuo to afford the title compound 65 (1.0 g, 52%) as a white solid: mp=74-76° C.; 1H NMR (CDCl3) δ 10.37 (s, 1H), 9.36 (m, 1H), 8.98 (m, 1H), 8.56 (m, 1H), 7.88 (m, 1H); LRMS (ESI) m/z calcd for C6H6N3 [M+H—N2]+ 120. found 120; HRMS (ESI) m/z calcd for C6H6N5 [M+H]+ 148.0623. found 148.0636; HPLC>99% (tR=3.44 min, 60 (A):40 (B): 0.009 (C); tR=2.71 min, 60 (A):40 (B): 0.02 (C)).

Provenance & Evidence