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

HRID 1166170Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1166170
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9ac846ac82824d0380d10e1389d08ed7
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06613775B1

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