1-(4-Cyano-pyridin-2-yl)-3-methyl-urea → 1-(4-Aminomethyl-pyridin-2-yl)-3-methyl-urea

HRID 602420Notes

Reaction equation

HRID 602420 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]([NH:12][CH3:13])=[O:11])[CH:4]=1)#[N:2]>C1COCC1.[Ni].CCOC(C)=O>[NH2:2][CH2:1][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]([NH:12][CH3:13])=[O:11])[CH:4]=1

Participants

5

Reactant 1

HCID 231188621-(4-Cyano-pyridin-2-yl)-3-methyl-urea

Product 1

HCID 231188611-(4-Aminomethyl-pyridin-2-yl)-3-methyl-ureaYield 233.6%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(4-cyano-pyridin-2-yl)-3-methyl-urea (12.0 g, 11.4 mmol) in THF (80 mL) was treated with Raney nickel (0.5 g) placed under a hydrogen atmosphere (atmospheric pressure) for 8 hours at rt. The reaction mixture was diluted with EtOAc, filtered over Celite® and concentrated in vacuo. The residue was purified by chromatography on silica gel (Gradient elution: 100% CH2Cl2 to 85%/15% CH2Cl2/MeOH) to give 1-(4-aminomethyl-pyridin-2-yl)-3-methyl-urea (4.8 g) as a solid.

Workup

  1. customfor 8 hours
  2. customat rt
  3. filtrationfiltered over Celite®
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on silica gel (Gradient elution: 100% CH2Cl2 to 85%/15% CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-c23010780b7241f5a70782aefa29db74
Source dataset
uspto-grants-2011_03
Patent number
US07906533B2

Reaction notes

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