Water → Tert-butyl (3-methyl-5-nitropyridin-2-yl)carbamate

Reaction equation

[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[C:12](=[O:15])([O-])[O-:13].[Cs+].[Cs+].O>CN(C=O)C>[CH3:8][C:7]1[C:2]([NH:1][C:12](=[O:15])[O:13][C:7]([CH3:8])([CH3:2])[CH3:6])=[N:3][CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[CH:6]=1

Participants

Procedure

2-Amino-3-methyl-5-nitropyridine (1 g, 6.5 mmol) and di-tert-butyl Bicarbonate (2.2 g, 9.8 mmol) were added in DMF (33 mL), then cesium carbonate (6.4 g, 19.6 mmol) at room temperature for 6 hours. Water (200 mL) was added, extracted with ethyl acetate (200 mL), second wash with brine (100 mL). The organic phase was dried by magnesium sulfate, filtered, concentrated and purified by column chromatography through a 25 gram Biotage SNAP KP-Sil™ silica gel cartridge eluting with 13% ethyl acetate/hexanes to give the title compound as a pale yellow solid.