Acetic Anhydride → 2-[2-(2-Fluoro-phenyl)-vinyl]-3-o-tolyl-3H-pteridin-4-one

HRID 1737250Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1737250
[CH3:1][C:2]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[C:10](=[O:19])[C:9]2[C:4](=[N:5][CH:6]=[CH:7][N:8]=2)[N:3]=1.[F:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH:23]=O.C(OC(=O)C)(=O)C>O1CCOCC1>[F:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH:23]=[CH:1][C:2]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[C:10](=[O:19])[C:9]2[C:4](=[N:5][CH:6]=[CH:7][N:8]=2)[N:3]=1

Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 67970o-FluorobenzaldehydeHCID 2107974(3H)-Pteridinone, 2-methyl-3-(o-tolyl)-

Produkt 1

HCID 697092452-[2-(2-Fluoro-phenyl)-vinyl]-3-o-tolyl-3H-pteridin-4-oneAusbeute 55,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of fused zinc chloride (0.17 g, 1.25 mmol), dioxane (15 mL), 2-methyl-3-(2-methyl-phenyl)-3H-pteridin-4-one (0.174 g, 0.69 mmol, preparation 8), and 2-fluorobenzaldehyde (0.22 mL, 2.07 mmol), and acetic anhydride 0.195 mL, 2.07 mmol) was refluxed overnight. The reaction was cooled and concentrated. The residual material was partitioned between saturated aqueous sodium bicarbonate and methylene chloride. The layers were carefully shaken and separated. The organic layer was washed with brine, dried and concentrated. The residue was flash chromatographed on silica gel (0.75×4 inches) with elution proceeding as follows: 50% ethyl acetate/hexane (300 mL), forerun; 60% ethyl acetate/hexane (400 mL). 2-[2-(2-Fluoro-phenyl)-vinyl]-3-o-tolyl-3H-pteridin-4-one (0.137 g, 55%) was isolated as a yellow crystalline solid. A sample was recrystallized from ethyl acetate.

Aufarbeitung

  1. temperaturewas refluxed overnight
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated
  4. customThe residual material was partitioned between saturated aqueous sodium bicarbonate and methylene chloride
  5. customseparated
  6. washThe organic layer was washed with brine
  7. customdried
  8. concentrationconcentrated
  9. customchromatographed on silica gel (0.75×4 inches) with elution proceeding

Quellen und Nachweise

ORD-Eintrag
ord-2596b366804648f7bf2b5860aa278aac
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05962457

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