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

HRID 1892214Notes

Reaction equation

HRID 1892214 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][CH2:8][C:9]#[C:10][C:11]1[CH:12]=[N:13][C:14]([CH3:20])=[C:15]([N+:17]([O-])=O)[CH:16]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6](=[O:21])[NH:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[N:13][C:14]([CH3:20])=[C:15]([NH2:17])[CH:16]=1)([CH3:3])([CH3:4])[CH3:2]

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-a16d672dfd7d4102a3ec580ddacca744
Source dataset
uspto-grants-2013_08
Patent number
US08507667B2

Reaction notes

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