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

HRID 1039073Notes

Reaction equation

HRID 1039073 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

5

Reactant 3

HCID 962WaterHCID 10796Cesium carbonateHCID 27344462-Amino-3-methyl-5-nitropyridine

Product 1

HCID 67962193Tert-butyl (3-methyl-5-nitropyridin-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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.

Workup

  1. extractionextracted with ethyl acetate (200 mL)
  2. washsecond wash with brine (100 mL)
  3. dry with materialThe organic phase was dried by magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by column chromatography through a 25 gram Biotage SNAP KP-Sil™ silica gel cartridge
  7. washeluting with 13% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-b5f4ed468b374c6ca6dbb68ca682fea9
Source dataset
uspto-grants-2013_10
Patent number
US08552022B2

Reaction notes

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