[CH3:1][N:2]([CH3:23])[C:3]([NH:5][C:6]1[CH:11]=[C:10]([O:12][C:13]2[C:14]([CH3:22])=[N:15][C:16]([N+:19]([O-])=O)=[CH:17][CH:18]=2)[CH:9]=[CH:8][N:7]=1)=[O:4].[NH4+].[Cl-]>CO.C1COCC1.CCOC(C)=O.[Zn]>[NH2:19][C:16]1[N:15]=[C:14]([CH3:22])[C:13]([O:12][C:10]2[CH:9]=[CH:8][N:7]=[C:6]([NH:5][C:3](=[O:4])[N:2]([CH3:23])[CH3:1])[CH:11]=2)=[CH:18][CH:17]=1
A mixture of 1,1-dimethyl-3-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)urea (0.500 g, 1.576 mmol) and NH4Cl (2.53 g, 47.3 mmol) in MeOH (10 mL) and THF (10 mL) was treated with zinc dust (1.030 g, 15.76 mmol) and stirred at RT for 0.5 h. The mixture was diluted with EtOAc, the solids removed via filtration, washed with EtOAc and the filtrate concentrated to dryness. The residue was treated with DCM, sonicated, the solids removed via filtration and the filtrate concentrated to dryness to afford 3-(4-((6-amino-2-methylpyridin-3-yl)oxy)pyridin-2-yl)-1,1-dimethylurea (510 mg, 113%). MS (ESI) m/z: 288.1 (M+H+).
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