4-Fluoroaniline → 2-Ethyl-3-(4-fluorophenyl)pyrido[2,3-d]pyrimidin-4(3H)-one

HRID 1264909Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1264909
[CH2:1]([C:3]1O[C:5](=[O:13])[C:6]2[CH:12]=[CH:11][CH:10]=[N:9][C:7]=2[N:8]=1)[CH3:2].[F:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1>C1(C)C=CC=CC=1>[CH2:1]([C:3]1[N:19]([C:18]2[CH:20]=[CH:21][C:15]([F:14])=[CH:16][CH:17]=2)[C:5](=[O:13])[C:6]2[CH:12]=[CH:11][CH:10]=[N:9][C:7]=2[N:8]=1)[CH3:2]

Komponenten

4

Edukt 2

HCID 97314-FluoroanilineHCID 186137472-Ethyl-4H-pyrido[2,3-d][1,3]oxazin-4-one

Produkt 1

HCID 186137392-Ethyl-3-(4-fluorophenyl)pyrido[2,3-d]pyrimidin-4(3H)-oneAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A suspension of the pyrido-oxazine (16) (0.5 g, 2.84 mmol) and 4-fluoroaniline (0.32 g, 2.84 mmol) in toluene (21 mL) was heated to reflux overnight. The solution was concentrated to dryness under reduced pressure and ethylene glycol (2 mL) and sodium hydroxide (5 mg) were added. The mixture was heated again to 120° C. for 4 h, and the ethylene glycol was distilled off under reduced pressure. The resulting dark brown solid was subjected to silica-gel column chromatography [eluent: Ethyl acetate:Hexane, 20:80, v/v→100:0, v/v] to give the title pyrido-pyrimidinone (17) (244 mg, 32%) as a beige solid:

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. concentrationThe solution was concentrated to dryness under reduced pressure and ethylene glycol (2 mL) and sodium hydroxide (5 mg)
  4. additionwere added
  5. distillationthe ethylene glycol was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-880af88b750e49a3bcb7a9499853eb9d
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06545005B1

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