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Water → 5-(5-(quinazolin-4-yloxy)pentyloxy)-2-(hydroxymethyl)-4H-pyran-4-one

HRID 2108856
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2108856
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([OH:11])=[N:3][CH:2]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25]1[C:26](=[O:33])[CH:27]=[C:28]([CH2:31][OH:32])[O:29][CH:30]=1.O>CN(C=O)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([O:11][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25]2[C:26](=[O:33])[CH:27]=[C:28]([CH2:31][OH:32])[O:29][CH:30]=2)=[N:3][CH:2]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 179758375-(5-Bromopentyloxy)-2-(hydroxymethyl)-4H-pyran-4-oneHCID 178517962HCID 178517962, Verbindung

Produkt 1

HCID 179757985-(5-(quinazolin-4-yloxy)pentyloxy)-2-(hydroxymethyl)-4H-pyran-4-oneAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel
2×

Versuchsvorschrift

Quinazolin-4-ol (1.0 g, 6.84 mmol) was dissolved in DMF (7 mL). Cs2CO3 (2.23 g, 6.84 mmol) was added at RT and the mixture was stirred for 10 min. A solution of 5-(5-bromo-pentyloxy)-2-hydroxymethyl-pyran-4-one 10 (1.90 g, 6.52 mmol) in DMF (7 mL) was added via syringe. This mixture was stirred at 50° C. for 2 h. Water (150 mL) was added and the mixture extracted with EtOAc (2×100 mL), washed with water (3×100 mL), brine (3×100 mL), dried over MgSO4, filtered and evaporated. The crude product was purified by column chromatography on silica using as eluent CH2Cl2:MeOH=95:5. 5-(5-(Quinazolin-4-yloxy)pentyloxy)-2-(hydroxymethyl)-4H-pyran-4-one 15 was obtained (0.61 g, 26% yield) as a pale yellow solid.

Aufarbeitung

  1. stirringThis mixture was stirred at 50° C. for 2 h
  2. extractionthe mixture extracted with EtOAc (2×100 mL)
  3. washwashed with water (3×100 mL), brine (3×100 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by column chromatography on silica using as eluent CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-ec877a2919ae4c9ca88a301d964f4269
Quelldatensatz
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07514432B2

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