Sodium Carbonate → Ethyl 8-Amino-3,6-dimethylimidazo[1,2-a]pyridin-2-carboxylate

HRID 1166170ノート

反応式

HRID 1166170 の反応式
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([CH3:9])=[CH:4][N:3]=1.[CH2:10]([O:12][C:13](=[O:19])[C:14](=O)[CH:15](Br)[CH3:16])[CH3:11].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[NH2:8][C:7]1[C:2]2[N:3]([C:15]([CH3:16])=[C:14]([C:13]([O:12][CH2:10][CH3:11])=[O:19])[N:1]=2)[CH:4]=[C:5]([CH3:9])[CH:6]=1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 107018255-Methylpyridine-2,3-diamineHCID 11117285Ethyl 3-bromo-2-oxobutanoate

生成物 1

HCID 22997462Ethyl 8-Amino-3,6-dimethylimidazo[1,2-a]pyridin-2-carboxylate収率 30%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of 2,3-diamino-5-methyl-pyridine (2.3 g, 19 mmol) and 3-bromo-2-oxo-butyric acid ethyl ester (4.3 g, 21 mmol) in ethanol (25 ml) was refluxed for 20 h. Sodium carbonate (2.6 g, 25 mmol) was added and the mixture was filtrated and the solids were washed with ethanol. The filtrate and washings were combined and evaporated under reduced pressure. The residue was dissolved in methylene chloride, washed twice with a sodium carbonate solution and twice with water. The organic layer was separated dried (Na2SO4) and evaporated under reduced pressure. Purification of the residue by column chromatography on silica gel using methylene chloride:methanol (9:1) as eluent gave 1.3 g (30%) of the title compound as an oil.

後処理

  1. filtrationthe mixture was filtrated
  2. washthe solids were washed with ethanol
  3. customevaporated under reduced pressure
  4. dissolutionThe residue was dissolved in methylene chloride
  5. washwashed twice with a sodium carbonate solution and twice with water
  6. customThe organic layer was separated
  7. dry with materialdried (Na2SO4)
  8. customevaporated under reduced pressure
  9. customPurification of the residue by column chromatography on silica gel

出典と根拠

ORDレコード
ord-9ac846ac82824d0380d10e1389d08ed7
出典データセット
uspto-grants-2003_09
特許番号
US06613775B1

反応ノート

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