Ethyl orthoformate → HCID 131734296, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl (2-aminopyridin-4-yl)acetate (18 mg, 0.087 mmol) in glacial acetic acid (1 mL) was added triethyl orthoformate (43 μL, 0.261 mmol) and sodium azide (17 mg, 0.261 mmol). The reaction mixture was heated at 80° C. for 3 hours in a sealed vial and then cooled to ambient temperature. Once cooled, water (1.5 mL) and solid sodium bicarbonate were added until a pH range of 6-7 was achieved. The aqueous layer was extracted with ethyl acetate (3×6 mL). The combined organic layers were then dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified via reverse phase reverse-phase HPLC (TMC Pro-Pac C18; 10-100% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient) to afford tert-butyl[2-(1H-tetrazol-1-yl)pyridin-4-yl]acetate: LC-MS: (M+H-28)+234.

Provenance & Evidence