[CH3:1][C:2]1[C:3]([NH2:8])=[N:4][CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.[I:14](O)(=O)(=O)=O.II.[O-]S([O-])(=S)=O.[Na+].[Na+]>O.CC(O)=O>[I:14][C:6]1[CH:7]=[C:2]([CH3:1])[C:3]([NH2:8])=[N:4][CH:5]=1To a solution of 3-methyl-2-pyridineamine (10 g) in a mixed solution of AcOH (60 mL), water (12 mL), and sulfuric acid (4.2 mL) was added periodic acid dehydrate (4.22 g) and iodine (9.39 g), and the mixture was heated at 80° C. for 2 hours. The reaction mixture was poured into 5% Na2S2O3 aq solution and extracted with ether. The organic layer was washed with 1N NaOH aq solution and brine, and dried over Na2SO4. The solvent was removed in vacuo and obtained residual solid was recrystallized with EtOH to give 5-iodo-3-methyl-2-pyridinamine (9.00 g) as pale yellow powder.
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