Triethylamine → 8-Amino-2,3,6-trimethylimidazo[1,2-a]pyridine

HRID 1386081Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1386081
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([CH3:9])=[CH:4][N:3]=1.Br[CH:11]([CH3:15])[C:12](=O)[CH3:13].C(N(CC)CC)C>C(O)C>[NH2:8][C:7]1[C:2]2[N:3]([C:11]([CH3:15])=[C:12]([CH3:13])[N:1]=2)[CH:4]=[C:5]([CH3:9])[CH:6]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 131422-Butanone, 3-bromo-2×HCID 107018255-Methylpyridine-2,3-diamine

Produkt 1

HCID 226726328-Amino-2,3,6-trimethylimidazo[1,2-a]pyridineAusbeute 37,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 2,3-diamino-5-methylpyridine (2.0 g, 16 mmol) in ethanol (100 ml) was added 3-bromo-2-butanon (2.4 g, 16 mmol). The reaction mixture was refluxed for 16 h. An additional amount of 3-bromo-2-butanon (1.0 g 6.7 mmol) and triethylamine (1.0 g, 9.9 mmol) were added and the mixture was refluxed for 2 h. The ethanol was evaporated under reduced pressure and the residue was treated with methylene chloride and a solution of bicarbonate. The organic layer was separated, dried over sodium sulfate and evaporated under reduced pressure. The oily residue was purified by column chromatography on silica gel, using methanol:methylene chloride (1:20) as eluent to give the desired product (1.05 g, 37%).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 16 h
  2. temperaturethe mixture was refluxed for 2 h
  3. customThe ethanol was evaporated under reduced pressure
  4. additionthe residue was treated with methylene chloride
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe oily residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-d537ac7a2dd643fb847a3f6a3f01079b
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06265415B1

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