Ethyl orthoformate → tert-butyl[2-(1H-tetrazol-1-yl)pyrimidin-5-yl]acetate

Participants

Reaction Steps

Trimethylsilyl trifluoroacetate (0.14 mL, 0.81 mmol) was added to a suspension of tert-butyl (2-aminopyrimidin-5-yl)acetate (100 mg, 0.478 mmol) in Ethyl acetate (1.5 mL). The reaction mixture was stirred at RT for 5 minutes and triethyl orthoformate (0.14 mL, 0.84 mmol) was added. The reaction mixture was stirred at RT for 5 minutes and azidotrimethylsilane (0.1 mL, 0.760 mmol) was added. The reaction mixture was stirred at RT overnight. The reaction mixture was diluted with EtOAc and washed with water and brine, dried (MgSO4), filtered and the solvent evaporated to afford the title compound: LC/MS (M+1)+ at 263 and (M+1-N2-tBu)+ at 179.

Provenance & Evidence