Sodium hydride → 3-Dibenzylamino-6,7-difluoro-1-cyclopropylmethyl-1H-quinazoline-2,4-dione

HRID 729399Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 729399
[CH2:1]([N:8]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[N:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][C:14]([F:21])=[C:15]([F:20])[CH:16]=2)[NH:11][C:10]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:33][CH:34]1[CH2:36][CH2:35]1>CN(C)C=O>[CH2:23]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[N:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][C:14]([F:21])=[C:15]([F:20])[CH:16]=2)[N:11]([CH2:33][CH:34]2[CH2:36][CH2:35]2)[C:10]1=[O:22])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 219790003-Dibenzylamino-6,7-difluoro-1H-quinazoline-2,4-dione

Produkt 1

HCID 219788423-Dibenzylamino-6,7-difluoro-1-cyclopropylmethyl-1H-quinazoline-2,4-dioneAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of 3-dibenzylamino-6,7-difluoro-1H-quinazoline-2,4-dione (Example 16) (0.43 g, 1.1 mmol) in 10 mL of N,N-dimethylformamide is added to a suspension of sodium hydride (0.05 g, 1.3 mmol) in 10 mL of N,N-dimethylformamide and stirred for 30 minutes. Bromomethylcyclopropane (0.16 mL, 1.6 mmol) is added, and the mixture is stirred at 25° C. for 18 hours. The reaction is quenched with 1 mL of water and concentrated in vacuo. The residue is dissolved in chloroform, washed with water, brine, and dried over magnesium sulfate. The solution is concentrated and purified via chromatography (SiO2, CHCl3) to give 0.33 g of the title compound as a solid. MS CI: m/z 448 (MH+).

Aufarbeitung

  1. stirringthe mixture is stirred at 25° C. for 18 hours
  2. customThe reaction is quenched with 1 mL of water
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue is dissolved in chloroform
  5. washwashed with water, brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationThe solution is concentrated
  8. custompurified via chromatography (SiO2, CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-cf4a3195a0894e2493e3ac2d5ce6d82d
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582627B2

Notizen zur Reaktion

Wird geladen…