Sodium Chloride → 5-Bromo-N,3-dimethylpyridin-2-amine

HRID 500717Notes

Reaction equation

HRID 500717 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:9])[C:5]([NH2:8])=[N:6][CH:7]=1.[H-].[Na+].I[CH3:13].[Na+].[Cl-]>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH3:9])[C:5]([NH:8][CH3:13])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1379342-Amino-5-bromo-3-methylpyridine

Product 1

HCID 183293675-Bromo-N,3-dimethylpyridin-2-amineYield 57.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 5-bromo-3-methylpyridin-2-amine (B-4-1) (3.7 g, 0.02 mol) in THF (50 mL) was added portionwise NaH (0.8 g, 0.02 mol) at 0° C. After the addition, the mixture was stirred at room temperature for about 0.5 hr, and cooled to 0° C. again. Iodomethane (2.8 g, 0.02 mol) was added slowly. The resulting mixture was allowed to rise to room temperature and stirred for 1 hr. TLC (EtOAc: Petroleum ether=1:4) showed that the reaction was complete. Saturated aqueous NaCl (10 mL) and EtOAc (10 mL) were added. The organic layer was concentrated and the residue was purified via a silica gel column eluted with EtOAc/Petroleum ether (1:8) to give 5-bromo-N,3-dimethylpyridin-2-amine (B-4-2) (2.3 g, 57.8%) as a white solid.

Workup

  1. additionAfter the addition
  2. temperaturecooled to 0° C. again
  3. customto rise to room temperature
  4. stirringstirred for 1 hr
  5. concentrationThe organic layer was concentrated
  6. customthe residue was purified via a silica gel column
  7. washeluted with EtOAc/Petroleum ether (1:8)

Sources & evidence

ORD record
ord-f71263ced667406c8b097622405b701e
Source dataset
uspto-grants-2010_08
Patent number
US07772246B2

Reaction notes

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