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Water → 2-(2,6-dimethyl-pyridin-4-yl)-7-fluoro-5-(2-pyrrolidin-1-yl-ethoxy)-3H-quinazolin-4-one

HRID 591844
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 591844
[N:1]1([CH2:6][CH2:7][OH:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:11][C:12]1[CH:17]=[C:16]([C:18]2[NH:27][C:26](=[O:28])[C:25]3[C:20](=[CH:21][C:22]([F:30])=[CH:23][C:24]=3F)[N:19]=2)[CH:15]=[C:14]([CH3:31])[N:13]=1.O>CN(C=O)C.C(O)(=O)C>[CH3:11][C:12]1[CH:17]=[C:16]([C:18]2[NH:27][C:26](=[O:28])[C:25]3[C:20](=[CH:21][C:22]([F:30])=[CH:23][C:24]=3[O:8][CH2:7][CH2:6][N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[N:19]=2)[CH:15]=[C:14]([CH3:31])[N:13]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 762881-PyrrolidineethanolHCID 1363480062-(2,6-dimethylpyridin-4-yl)-5,7-difluoro-3H-quinazolin-4-one

Produkt 1

HCID 1363480592-(2,6-dimethyl-pyridin-4-yl)-7-fluoro-5-(2-pyrrolidin-1-yl-ethoxy)-3H-quinazolin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176
Acetic Acid
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-pyrrolidin-1-yl-ethanol (5.09 g, 44.2 mmol) in DMF (10 mL) was added sodium hydride (60% suspension in mineral oil, 0.88 g, 22.1 mmol) in small portions and the reaction mixture was stirred at room temperature for 30 minutes. To this mixture was added 2-(2,6-dimethyl-pyridin-4-yl)-5,7-difluoro-3H-quinazolin-4-one (0.63 g, 2.21 mmol) and the reaction mixture was stirred at room temperature for 16 hours. Water (20 mL) was added, and the mixture was neutralized to pH approximately 6 with acetic acid. Solvent was evaporated, the residue was dissolved in ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo. Crude compound was purified by the Simpliflash system (0-4% methanol in CH2Cl2 as eluent) to afford 2-(2,6-dimethyl-pyridin-4-yl)-7-fluoro-5-(2-pyrrolidin-1-yl-ethoxy)-3H-quinazolin-4-one as a yellow solid. Yield: 0.61 g (72%).

Aufarbeitung

  1. stirringthe reaction mixture was stirred at room temperature for 16 hours
  2. customSolvent was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customCrude compound was purified by the Simpliflash system (0-4% methanol in CH2Cl2 as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-8e8b23bc08034d8097db0bd20a5cfd9a
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09238640B2

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