Water → HCID 67354691, compound

HRID 1846147Notes

Reaction equation

HRID 1846147 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([Br:9])=[C:4]([CH3:10])[N:3]=1.[C:11]1(C)[CH:16]=[CH:15][C:14](S(O)(=O)=O)=[CH:13][CH:12]=1.O>C1(C)C=CC=CC=1>[CH3:14][C:13]1[N:1]([C:2]2[CH:7]=[C:6]([CH3:8])[C:5]([Br:9])=[C:4]([CH3:10])[N:3]=2)[C:16]([CH3:15])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 110308555-Bromo-4,6-dimethylpyridin-2-amine

Product 1

HCID 67354691HCID 67354691, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution containing 2.76 g (13.75 mmol) of 2-amino-5-bromo-4,6-dimethylpyridine (13) in 25 mL of toluene were added 2.02 mL (17.18 mmol) of 2,5-hexadienone followed by 130 mg (0.68 mmol) of p-toluene sulfonic acid. The reaction mixture was stirred at reflux overnight under argon atmosphere. The reaction mixture was poured into 150 mL of water and then extracted with a portion of 200 mL of ethyl acetate. The organic solution was washed with a portion of 150 mL of brine, dried (MgSO4) and then concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column. Elution with hexanes-ethyl acetate 5:1 gave the expected product as an orange oil: yield 2.37 g (62%). 1H-NMR (CDCl3) δ 6.93 (s, 1H), 5.88 (s, 2H), 2.70 (s, 3H), 2.47 (s, 3H), 2.12 (s, 6H); 13C-NMR (CDCl3) δ 157.35, 149.32, 128.42, 122.49, 121.22, 25.58, 23.41, 13.10.

Workup

  1. temperatureat reflux overnight under argon atmosphere
  2. extractionextracted with a portion of 200 mL of ethyl acetate
  3. washThe organic solution was washed with a portion of 150 mL of brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under diminished pressure
  6. customThe residue was purified by chromatography on a silica gel column
  7. washElution with hexanes-ethyl acetate 5:1

Sources & evidence

ORD record
ord-62b9024bc46b4c4d8383375a42cb9a6f
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

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