Triethylamine → FK 360

HRID 4680

Reaktionsgleichung

Reaktionsgleichung von HRID 4680
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10]([C:21](=O)[CH3:22])=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)=[O:9])[CH2:4][CH2:3]1.Cl.[C:25]([NH2:33])(=[NH:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(CC)CC)C>C(O)CCC>[CH3:22][C:21]1[N:33]=[C:25]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:32]=[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:10]=1[C:8]([N:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1)=[O:9]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 80289Benzamidine, hydrochlorideHCID 54532914HCID 54532914, Verbindung

Produkt 1

HCID 3025486FK 360

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

A mixture of 2-(4-methylpiperazin-1-ylcarbonyl)-1-(3-nitrophenyl)-1-buten-3-one (20 g), benzamidine hydrochloride (9.9 g) and triethylamine (11.4 ml) in n-butanol (200 ml) was refluxed for 2 hours. After evaporating the solvent, the residue was dissolved in a suspension of water (200 ml) and chloroform (200 ml). The separated organic layer was washed with saturated aqueous sodium chloride and dried over magnesium sulfate. To this solution was added activated manganese dioxide (120 g) and the mixture was refluxed for 1 hour with stirring vigorously. After cooling to a room temperature, manganese dioxide was filtered off. The filtrate was evaporated in vacuo, and the residue was subjected to column chromatography on alumina (200 g) eluting with chloroform. The fractions containing the object compound were combined and concentrated under reduced pressure. The crystals were recrystallized from diethyl ether to give 6-methyl-5-(4-methylpiperazin-1-ylcarbonyl)-4-(3-nitrophenyl)-2-phenylpyrimidine.

Aufarbeitung

  1. temperaturewas refluxed for 2 hours
  2. customAfter evaporating the solvent
  3. dissolutionthe residue was dissolved in a suspension of water (200 ml) and chloroform (200 ml)
  4. washThe separated organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. additionTo this solution was added activated manganese dioxide (120 g)
  7. temperaturethe mixture was refluxed for 1 hour
  8. filtrationmanganese dioxide was filtered off
  9. customThe filtrate was evaporated in vacuo
  10. washeluting with chloroform
  11. additionThe fractions containing the object compound
  12. concentrationconcentrated under reduced pressure
  13. customThe crystals were recrystallized from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-8bcae92e09434b79989104d97d819e5f
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04727073

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