[NH2:1][C:2]1[C:3]([CH3:13])=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[N:6][CH:7]=1.[CH:14](OCC)(OCC)OCC.[N-:24]=[N+:25]=[N-:26].[Na+]>C(O)(=O)C.[Cl-].[Na+].O>[CH3:13][C:3]1[C:2]([N:1]2[CH:14]=[N:26][N:25]=[N:24]2)=[CH:7][N:6]=[C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:4]=1Methyl 2-(5-amino-4-methylpyridin-2-yl)acetate (90 mg, 0.499 mmol) was stirred in acetic acid (3 ml) then added triethyl orthoformate (0.166 ml, 0.999 mmol) and sodium azide (58.4 mg, 0.899 mmol). The mixture was stirred at 80° C. for 3 hrs then diluted with brine and extracted with ethyl acetate. The organic layer was dried over Na2SO4, filtered and evaporated to dryness. The residue was chromatographed thru 40 g ISCO Redi-sep column and eluted with 5% MeOH/DCM to yield methyl 2-(4-methyl-5-(1H-tetrazol-1-yl)pyridin-2-yl)acetate: 1H-NMR (500 MHz, CDCl3) δ ppm 8.867 (s, 1H), 8.527 (s, 1H), 7.438 (s, 1H), 3.963 (s, 2H), 3.790 (s, 3H), 2.308 (s, 3H).
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