Br[C:2]1[N:7]=[C:6]([NH:8][C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[O:10])[C:5]([O:15][CH3:16])=[CH:4][CH:3]=1.[NH3:17]>C(O)CO>[NH3:7].[CH3:9][OH:10].[NH2:17][C:2]1[N:7]=[C:6]([NH:8][C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[O:10])[C:5]([O:15][CH3:16])=[CH:4][CH:3]=1A pressure tube was charged with 6-bromo-2-(tert-butylcarbonyl)amino-3-methoxypyridine (34) (0.287 g), ethylene glycol (3 mL) and Cu2O (0.028 g) and cooled to −78° C. To this mixture, 1 mL of liquid ammonia was collectyed (at −78° C.), the pressure tube was sealed and then stirred at room temperature for 24 hours. The reaction mixture was again cooled to −78° C., the seal was removed and the reaction mixture diluted with water (10 mL). The aqueous solution was extracted with ethyl acetate (3×50 mL), dried over anhydrous sodium sulfate and solvent was removed under a reduced pressure. The resulting residue was chromatographed (silica gel, CH2Cl2 then 1% 2N NH3/MeOH in CH2Cl2 to obtain 6-amino-2-(tert-butylcarbonyl)amino-3-methoxypyridine (35). LCMS: purity: 94%; MS (m/z): 224 (MH+).
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