HCID 70881450, compound → Tert-butyl [3-(5-amino-6-methylpyridin-3-yl)propyl]carbamate

HRID 2388015Notes

Reaction equation

HRID 2388015 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][C:3]=1[N+:19]([O-])=O>CO.[OH-].[OH-].[Pd+2]>[NH2:19][C:3]1[CH:4]=[C:5]([CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:15])[CH3:17])[CH:6]=[N:7][C:2]=1[CH3:1]

Participants

4

Reactant 1

HCID 70881450HCID 70881450, compound

Product 1

HCID 68222687Tert-butyl [3-(5-amino-6-methylpyridin-3-yl)propyl]carbamateYield 109.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl [3-(6-methyl-5-nitropyridin-3-yl)prop-2-yn-1-yl]carbamate (2.98 g, 10.2 mmol) in MeOH (100 mL) was added palladium hydroxide on carbon (0.72 g). The reaction vessel was flushed with H2 and then the reaction mixture was allowed to stir at rt under an atmosphere of hydrogen overnight. The reaction mixture was filtered over a pad of Celite® and the filtrate was concentrated to give tert-butyl [3-(5-amino-6-methylpyridin-3-yl)propyl]carbamate (2.97 g, >99%) as a yellow oil. LCMS (FA): Rt=0.85 min, m/z=266.0 (M+H).

Workup

  1. customThe reaction vessel was flushed with H2
  2. filtrationThe reaction mixture was filtered over a pad of Celite®
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9525b542d29747c8b93e5ad331ad9242
Source dataset
uspto-grants-2012_09
Patent number
US08268992B2

Reaction notes

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