Ethyl orthoformate → ethyl 2-(6-methyl-5-(1H-tetrazol-1-yl)pyridin-2-yl)acetate

Participants

Reaction Steps

Trimethylsilyl trifluoroacetate (1.010 ml, 5.85 mmol) was added to a suspension of ethyl 2-(5-amino-6-methylpyridin-2-yl)acetate (710 mg, 3.66 mmol) in ethyl acetate (20 ml). The mixture was stirred for 5 mins then added triethyl orthoformate (1.096 ml, 6.58 mmol). Stirred for another 5 mins then added azidotrimethylsilane (0.817 ml, 6.21 mmol). The reaction was stirred overnight. The reaction was poured into brine and extracted with ethyl acetate. The ethyl acetate was separated, dried over Na2SO4, filtered and concentrated. The residue was purified by chromatography through 120 g ISCO Redi-Sep column and eluted with 5% MeOH/DCM to yield ethyl 2-(6-methyl-5-(1H-tetrazol-1-yl)pyridin-2-yl)acetate.

Provenance & Evidence