Ethyl Acetate → Tert-butyl 4-(2,3-diaminopyridin-4-yloxy)phenylcarbamate

HRID 1402987Notes

Reaction equation

HRID 1402987 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([O:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:14][CH:13]=2)[CH:5]=[CH:4][N:3]=1.C(OCC)(=O)C>C(O)C.[Pd]>[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([O:11][C:12]2[CH:13]=[CH:14][C:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[CH:16][CH:17]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 42626044Tert-butyl 4-(2-amino-3-nitropyridin-4-yloxy)phenylcarbamate

Product 1

HCID 42625416Tert-butyl 4-(2,3-diaminopyridin-4-yloxy)phenylcarbamateYield 88.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1.56 g (4.5 mmol) of tert-butyl 4-(2-amino-3-nitropyridin-4-yloxy)phenylcarbamate are dissolved in 300 ml of a 1:1 ethanol:ethyl acetate mixture. The solution was mixed with H2 was passed through a cartridge containing Pd/C in a H-cube apparatus, then was evaporated to provide 1.26 g (88% yield) of tert-butyl 4-(2,3-diaminopyridin-4-yloxy)phenylcarbamate as a white foamy solid.

Workup

  1. additionThe solution was mixed with H2
  2. customwas evaporated

Sources & evidence

ORD record
ord-9b0c571d96a24984b3f1f4c0232fd67b
Source dataset
uspto-grants-2014_12
Patent number
US08912191B2

Reaction notes

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