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

HRID 1180205Notes

Reaction equation

HRID 1180205 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-0f00127363bc4bb295861ea7393bf204
Source dataset
uspto-grants-2007_10
Patent number
US07279489B2

Reaction notes

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