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Acetic Anhydride → HCID 69710341, Verbindung

HRID 430504
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 430504
O1CCOCC1.[CH3:7][C:8]1[N:9]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])[C:10](=[O:17])[C:11]2[S:16][CH:15]=[CH:14][C:12]=2[N:13]=1.C(OC(=O)C)(=O)C.[N:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH:38]=O>C(=O)(O)[O-].[Na+]>[CH3:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[N:9]1[C:10](=[O:17])[C:11]2[S:16][CH:15]=[CH:14][C:12]=2[N:13]=[C:8]1[CH:7]=[CH:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][N:32]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 7918Acetic AnhydrideHCID 142732-PyridinecarboxaldehydeHCID 312751,4-DioxaneHCID 9016182-Methyl-3-(2-methylphenyl)thieno[3,2-d]pyrimidin-4-one

Produkt 1

HCID 69710341HCID 69710341, VerbindungAusbeute 70,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 516892
Sodium Bicarbonate
Lösungsmittel

Versuchsvorschrift

To a mixture of fused zinc chloride (2.13 g, 15.6 mmol) and dioxane (75 mL), 2-methyl-3-(2-methylphenyl)-3H-thieno[3,2-d]pyrimidin-4-one (2.0 g, 7.81 mmol, preparation 2), and acetic anhydride (2.2 mL, 23.4 mmol) was added 2-pyridine carboxaldehyde (2.2 mL, 23.4 mmol). The reaction was refluxed 1.5 hours, cooled to ambient temperature, and diluted with aqueous sodium bicarbonate. The mixture was extracted with ethyl acetate and the organic extracts were washed with water and brine, dried over sodium sulfate and concentrated to leave a dark residue. This material was flash chromatographed on silica gel (45×125 mm). Elution with 20% ethyl acetate/hexane removed an unweighed impurity. Continued elution with 40% ethyl acetate/hexane gave a sticky yellow foam. The foam was triturated with 5% ethyl acetate/hexane to yield 1.9 g (70%) of 3-(2-methyl-phenyl)-2-[2-pyrid-2-yl-vinyl]-3H-thieno[3,2-d]pyrimidin-4-one as a yellow solid.

Aufarbeitung

  1. temperatureThe reaction was refluxed 1.5 hours
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic extracts were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customto leave a dark residue
  7. customchromatographed on silica gel (45×125 mm)
  8. washElution with 20% ethyl acetate/hexane
  9. customremoved an unweighed impurity
  10. washelution with 40% ethyl acetate/hexane
  11. customgave a sticky yellow foam
  12. customThe foam was triturated with 5% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-66d15f5455684240bd6ba2461126fb75
Quelldatensatz
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06323208B1

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