Sodium hydride → 2-Butyl-6-methyl-3-[[4-(2-cyanopyridin-3-yl)phenyl]methyl]quinazolin-4(3H)-one

HRID 373129Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 373129
[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[N:14]=1)=[CH:11][C:10]([CH3:16])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4].[H-].[Na+].[C:19]([C:21]1[C:26]([C:27]2[CH:32]=[CH:31][C:30]([CH2:33]Br)=[CH:29][CH:28]=2)=[CH:25][CH:24]=[CH:23][N:22]=1)#[N:20].[NH4+].[Cl-]>CN(C=O)C.[Cl-].[Na+].O>[CH2:1]([C:5]1[N:14]([CH2:33][C:30]2[CH:29]=[CH:28][C:27]([C:26]3[C:21]([C:19]#[N:20])=[N:22][CH:23]=[CH:24][CH:25]=3)=[CH:32][CH:31]=2)[C:13](=[O:15])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH3:16])[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 183845143-[4-(Bromomethyl)phenyl]-2-pyridinecarbonitrileHCID 178441839HCID 178441839, Verbindung

Produkt 1

HCID 198115132-Butyl-6-methyl-3-[[4-(2-cyanopyridin-3-yl)phenyl]methyl]quinazolin-4(3H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of 2-butyl-6-methylquinazolin-4(1H)-one (1.0 eq.) from Example 1 Step B in DMF at rt is added NaH (1.5 eq. of an 80% dispersion in oil). After 20 min, 2-cyano-3-(4-bromomethylphenyl)pyridine (1.2 eq.) is added and the mixture is stirred at rt for 3 h. Brine (100 mL) and aqueous NH4Cl (40 mL) are added and the product is extracted with EtOAc. Purification by flash chromatography gives the above titled compound.

Aufarbeitung

  1. extractionthe product is extracted with EtOAc
  2. customPurification by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-58dae8270e5940adaf96ffe1afb7a2b3
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05162325

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