Sodium Hydroxide → 3-Amino-2-bromo-4,6-dimethylpyridine

HRID 1271570ノート

反応式

HRID 1271570 の反応式
Cl[C:2]1[C:7]([NH2:8])=[C:6]([CH3:9])[CH:5]=[C:4]([CH3:10])[N:3]=1.P(Br)(Br)[Br:12].[OH-].[Na+]>C1(C)C=CC=CC=1>[Br:12][C:2]1[C:7]([NH2:8])=[C:6]([CH3:9])[CH:5]=[C:4]([CH3:10])[N:3]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 24614Phosphorus tribromideHCID 105111202-Chloro-4,6-dimethylpyridin-3-amine

生成物 1

HCID 20493073-Amino-2-bromo-4,6-dimethylpyridine収率 38%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of 1.80 g (11.0 mmol) of 2-chloro-4,6-dimethyl-pyridin-3-ylamine (prepared as described in J. M. Klunder et al. J. Med. Chem., 35, 1992, 1887-1897) in toluene (10 ml) was added PBr3 (18 ml). The reaction mixture was stirred for 48 h under reflux. After cooling the reaction mixture, it was poured onto ice, basified with NaOH 2 M solution (400 ml) and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were washed with brine, dried over Na2SO4, filtered and evaporated. The crude residue was purified by flash chromatography (cyclohexane/ethyl acetate 7:3) to yield 2.31 g (38%) of 2-bromo-4,6-dimethyl-pyridin-3-ylamine containing small amount of 2-chloro-4,6-dimethyl-pyridin-3-ylamine as a yellow oil.

後処理

  1. temperatureunder reflux
  2. temperatureAfter cooling the reaction mixture, it
  3. additionwas poured onto ice
  4. extractionthe aqueous phase was extracted twice with ethyl acetate
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude residue was purified by flash chromatography (cyclohexane/ethyl acetate 7:3)

出典と根拠

ORDレコード
ord-9a6140d8aa2b41f19b7bf4fccb55939f
出典データセット
uspto-grants-2007_04
特許番号
US07205411B2

反応ノート

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