Acetic Acid → 5-Iodo-N,N-dimethylpyridin-2-amine

HRID 2109192Notes

Reaction equation

HRID 2109192 reaction equation
NC1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][N:3]=1.[H-].[Na+].IC.CC(O)=O.[CH3:17][N:18]([CH:20]=O)[CH3:19]>CCOC(C)=O>[I:8][C:5]1[CH:6]=[CH:7][C:20]([N:18]([CH3:19])[CH3:17])=[N:3][CH:4]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 885792-Pyridinamine, 5-iodo-

Product 1

HCID 234385795-Iodo-N,N-dimethylpyridin-2-amine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-amino-5-iodopyridine (1.00 g; 4.55 mmol) in 10 mL of DMF was added 545 mg of 60% NaH (13.6 mmol) and 0.85 mL of iodomethane (13.6 mmol). The mixture was stirred for 14 h, and the mixture was neutralized with 1M HOAc. The mixture was extracted with Et2O, the extract was washed with water and brine, dried with MgSO4, filtered, and concentrated. Chromatography (0-25% EtOAc in hexanes) provided 700 mg (2.82 mmol) of (5-iodo-pyridin-2-yl)-dimethyl-amine.

Workup

  1. extractionThe mixture was extracted with Et2O
  2. washthe extract was washed with water and brine
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-80fed01558de43fd9487a99ecb0df7ea
Source dataset
uspto-grants-2009_04
Patent number
US07514458B2

Reaction notes

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