[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[NH:4][N:3]=1.[H-].[Na+].[N+]([C:17]1[CH:22]=[CH:21][N+:20]([O-:23])=[CH:19][CH:18]=1)([O-])=O>CN(C)C=O>[NH2:11][C:9]1[N:8]=[CH:7][N:6]=[C:5]2[N:4]([C:17]3[CH:22]=[CH:21][N+:20]([O-:23])=[CH:19][CH:18]=3)[N:3]=[C:2]([I:1])[C:10]=12A solution of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (5.00 g, 0.019 mol) in N,N-dimethylformamide (50 mL) was reacted with 60% sodium hydride in oil (0.92 g, 0.023 mol) at ambient temperature. The mixture was stirred for 15 minutes, and 4-nitropyridine-N-oxide (5.37 g, 0.038 mol) was added. The mixture was heated at 100° C. for 18 hours. The precipitate which formed was filtered, washing with N,N-dimethylformamide and ethyl acetate to give 4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-pyridiniumolate (3.79 g, 0.011 mol) as a tan solid:
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