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Tetrahydro-4H-pyran-4-ol → 7-Benzyloxy-5-tetrahydropyran-4-yloxy-3,4-dihydroquinazolin-4-one

HRID 1826288
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1826288
N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.[CH2:17]([O:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29](=[O:43])[N:30](COC(=O)C(C)(C)C)[CH:31]=[N:32]2)=[C:27]([OH:44])[CH:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O[CH:46]1[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1>C(Cl)Cl>[CH2:17]([O:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29](=[O:43])[NH:30][CH:31]=[N:32]2)=[C:27]([O:44][CH:46]2[CH2:51][CH2:50][O:49][CH2:48][CH2:47]2)[CH:26]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 74956Tetrahydro-4H-pyran-4-olHCID 97268Di-tert-butyl azodicarboxylateHCID 119746277-Benzyloxy-5-hydroxy-3-pivaloyloxymethyl-3,4-dihydroquinazolin-4-one

Produkt 1

HCID 1358309117-Benzyloxy-5-tetrahydropyran-4-yloxy-3,4-dihydroquinazolin-4-oneAusbeute 79,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

Di-tert-butyl azodicarboxylate (16.3 g) was added portionwise to a stirred mixture of 7-benzyloxy-5-hydroxy-3-pivaloyloxymethyl-3,4-dihydroquinazolin-4-one (17 g), 4-hydroxytetrahydropyran (5.4 g) and methylene chloride (200 ml) that had been cooled to 5° C. The mixture was allowed to warm to ambient temperature and was stirred for 2 hours. The mixture was evaporated and the residue was dissolved in a saturated methanolic ammonia solution. The resultant mixture was stirred at ambient temperature for 16 hours. The mixture was evaporated and the residue was triturated under diethyl ether. The solid so obtained was dried under vaccuum to give 7-benzyloxy-5-tetrahydropyran-4-yloxy-3,4-dihydroquinazolin-4-one (12.5 g); NMR Spectrum: (DMSOd6) 1.6–1.7 (m, 2H), 1.85–1.95 (m, 2H), 3.5 (m, 2H), 3.9 (m, 2H), 4.75 (m, 1H), 5.22 (s, 2H), 6.7 (d, 1H), 6.8 (d, 1H), 7.3–7.5 (m, 5H), 7.9 (s, 1H); Mass Spectrum: M+H+ 353.

Aufarbeitung

  1. temperatureto warm to ambient temperature
  2. customThe mixture was evaporated
  3. dissolutionthe residue was dissolved in a saturated methanolic ammonia solution
  4. stirringThe resultant mixture was stirred at ambient temperature for 16 hours
  5. customThe mixture was evaporated
  6. customthe residue was triturated under diethyl ether
  7. customThe solid so obtained
  8. customwas dried under vaccuum

Quellen und Nachweise

ORD-Eintrag
ord-785db5eefdad4038ab4585be386fbdae
Quelldatensatz
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07049438B2

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