Tert-butyl(2-methoxy-5-nitropyridin-3-yl)methylcarbamate → Tert-butyl(5-amino-2-methoxypyridin-3-yl)methylcarbamate

HRID 1772893Notes

Reaction equation

HRID 1772893 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][C:9]1[C:10]([O:18][CH3:19])=[N:11][CH:12]=[C:13]([N+:15]([O-])=O)[CH:14]=1)([CH3:4])([CH3:3])[CH3:2]>CO.C(Cl)Cl.[Pd]>[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][C:9]1[C:10]([O:18][CH3:19])=[N:11][CH:12]=[C:13]([NH2:15])[CH:14]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 131734692Tert-butyl(2-methoxy-5-nitropyridin-3-yl)methylcarbamate

Product 1

HCID 131734691Tert-butyl(5-amino-2-methoxypyridin-3-yl)methylcarbamateYield 84.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

10% Pd/C (1 g) was added to a solution of tert-butyl(2-methoxy-5-nitropyridin-3-yl)methylcarbamate (9.8 g, 34.6 mmol) in MeOH (150 mL) and DCM (75 mL) and the mixture stirred at rt for 7 h under an atmosphere of H2. The reaction mixture was then filtered through celite and washed with MeOH and the filtrate concentrated in vacuo. Purification by flash column chromatography eluting with 2:1 to 1:1 heptane-EtOAc yielded the title compound (7.4 g, 29.2 mmol) as a tan solid.

Workup

  1. filtrationThe reaction mixture was then filtered through celite
  2. washwashed with MeOH
  3. concentrationthe filtrate concentrated in vacuo
  4. customPurification by flash column chromatography
  5. washeluting with 2:1 to 1:1 heptane-EtOAc

Sources & evidence

ORD record
ord-a7450b28f5af43a794aff2a2b43da89e
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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