Dimethylamine → 5-bromo-N,N-dimethylpyridin-2-amine

HRID 1358051Notes

Reaction equation

HRID 1358051 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH3:9][NH:10][CH3:11]>O1CCCC1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([N:10]([CH3:11])[CH3:9])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 693532,5-Dibromopyridine

Product 1

HCID 38030415-bromo-N,N-dimethylpyridin-2-amineYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,5-dibromopyridine (11.84 g, 50.0 mmol) in 2.0 M solution of dimethylamine in tetrahydrofuran (100 mL) in a sealed tube was heated at 120° C. for 12 hours. The reaction was quenched with ethyl acetate and washed with water. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The residue was then purified by chromatography (SiO2, 10-15% ethyl acetate/hexane) to provide the title compound (8.67 g, 86% yield): 1H NMR (CDCl3) 8.16 (d, 1H), 7.49 (dd, 1H), 6.41 (d, 1H), 3.05 (s, 6H); ES-MS m/z 201 [M+H]+.

Workup

  1. customThe reaction was quenched with ethyl acetate
  2. washwashed with water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was then purified by chromatography (SiO2, 10-15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c5e05515688e492290dc611c8fb8be0b
Source dataset
uspto-grants-2003_07
Patent number
US06593322B1

Reaction notes

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