4-Hydroxymethylpyridine → 7-(4-Pyridylmethoxy)-3,4-dihydroquinazolin-4-one

HRID 279543

Reaktionsgleichung

Reaktionsgleichung von HRID 279543
[H-].[Na+].[OH:3][CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1.F[C:12]1[CH:21]=[C:20]2[C:15]([C:16](=[O:22])[NH:17][CH:18]=[N:19]2)=[CH:14][CH:13]=1>C1COCC1>[N:8]1[CH:9]=[CH:10][C:5]([CH2:4][O:3][C:12]2[CH:21]=[C:20]3[C:15]([C:16](=[O:22])[NH:17][CH:18]=[N:19]3)=[CH:14][CH:13]=2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 114724-HydroxymethylpyridineHCID 24758Sodium hydrideHCID 1353984967-Fluoroquinazolin-4(3H)-one

Produkt 1

HCID 1356711817-(4-Pyridylmethoxy)-3,4-dihydroquinazolin-4-oneAusbeute 73,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Sodium hydride (0.72 g of a 60% suspension in mineral oil, 18 mmol) was added to a solution of 4-hydroxymethylpyridine (4 g, 36 mmol) in THF (30 ml) and the mixture heated at reflux for 15 minutes. 7-Fluoro-3,4-dihydroquinazolin-4-one (1 g, 6 mmol), (J. Chem. Soc. section B 1967, 449), was added, the THF was removed by evaporation, and the mixture was heated at 120° C. for 30 minutes. The mixture was allowed to cool, diluted with water (40 ml) and was adjusted to pH8 with concentrated hydrochloric acid. The resulting precipitate was collected by filtration, washed with water, then ether and dried under vacuum to give 7-(4-pyridylmethoxy)-3,4-dihydroquinazolin-4-one (1.12 g, 71%).

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureat reflux for 15 minutes
  3. customthe THF was removed by evaporation
  4. temperatureto cool
  5. additiondiluted with water (40 ml)
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with water
  8. dry with materialether and dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c6c09be9b5234091846e359d2e745dfc
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06362336B1

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