4-Aminopyridine → HCID 66893771, compound

HRID 252753Notes

Reaction equation

HRID 252753 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH2:7])=[CH:3][CH:2]=1.[CH3:8][S:9][C:10](SC)=[CH:11][C:12]#[N:13].[H-].[Na+]>CN(C=O)C>[CH3:8][S:9][C:10]([NH:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)=[CH:11][C:12]#[N:13]

Participants

5

Reactant 3

HCID 17274-AminopyridineHCID 24758Sodium hydrideHCID 53254452-Propenenitrile, 3,3-bis(methylthio)-

Product 1

HCID 66893771HCID 66893771, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of pyridin-4-ylamine (1.0 g, 11.0 mmol) and 3,3-Bis-methylsulfanyl-acrylonitrile (2.05 g, 12.6 mmol) in DMF at room temperature, was added powdered 4 A molecular sieves. The mixture was stirred for 1 hr. Subsequently the mixture was cooled to 0° C., 60% NaH dispersion in oil (0.92 g, 23.0 mmol) was added portionwise over 1 hr. and it was stirred at 0° C. for an additional 2 hrs. The cold bath was removed and the mixture was stirred at room temperature for 20 hrs. DMF was removed in vacuo and the crude was purified by column chromatography (gradient of EtOAc to 25% MeOH/EtOAc) to afford the desired product as an off-white solid (1.9 g, 89%).

Workup

  1. stirringand it was stirred at 0° C. for an additional 2 hrs
  2. customThe cold bath was removed
  3. stirringthe mixture was stirred at room temperature for 20 hrs
  4. customDMF was removed in vacuo
  5. customthe crude was purified by column chromatography (gradient of EtOAc to 25% MeOH/EtOAc)

Sources & evidence

ORD record
ord-3960bf7110f9479697840ab1c7502997
Source dataset
uspto-grants-2011_01
Patent number
US07868204B2

Reaction notes

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