Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:11][CH2:12][CH2:13][CH2:14][OH:15])[C:5]([CH3:16])=[C:4]([CH3:17])[N:3]=1.[N-:18]=[N+:19]=[N-:20].[Na+].O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].C(#N)C.O>CN(C=O)C>[CH3:17][C:4]1[N:3]2[N:18]=[N:19][N:20]=[C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:11][CH2:12][CH2:13][CH2:14][OH:15])[C:5]=1[CH3:16]A mixture of 3-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]propan-1-ol (12.4 g, 47.8 mmol), sodium azide (6.20 g, 95.5 nmnol), and cerium (III) chloride heptahydrate (8.90 g, 23.9 inmol) in 9:1 acetonitrile/water (160 mL) was heated at reflux for 16 hours, then was allowed to cool to room temperature. DMF was added and the mixture was filtered. The filter cake was washed with DMF. The filtrate was concentrated under reduced pressure to give an orange solid that was triturated with ethyl acetate to yield 9.60 g of 3-[(5,6-dimethyl-8-nitrotetraazolo[1,5-a]pyridin-7-yl)amino]propan-1-ol as a yellow solid.
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