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

HRID 373125Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 373125
[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+].[Na].[C:20]([C:22]1[CH:23]=[N:24][CH:25]=[CH:26][C:27]=1[C:28]1[CH:33]=[CH:32][C:31]([CH2:34]Br)=[CH:30][CH:29]=1)#[N:21]>CN(C=O)C.C(Cl)Cl.CC(O)=O>[CH2:1]([C:5]1[N:14]([CH2:34][C:31]2[CH:30]=[CH:29][C:28]([C:27]3[CH:26]=[CH:25][N:24]=[CH:23][C:22]=3[C:20]#[N:21])=[CH:33][CH:32]=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

8

Edukt 4

HCID 24758Sodium hydrideHCID 5360545SodiumHCID 183848873-Cyano-4-(4-bromomethylphenyl)pyridineHCID 178441839HCID 178441839, Verbindung

Produkt 1

HCID 198115062-Butyl-6-methyl-3-[[4-(3-cyanopyridin-4-yl)phenyl]methyl]quinazolin-4(3H)-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-butyl-6-methylquinazolin-4(1H)-one (1.0 eq.) from Example 1 in DMF at rt is added NaH (1.0 eq.) to generate the sodium salt. After 20 min, 3-cyano-4-(4-bromomethyl phenyl)pyridine (1 mL of a 2M solution in CH2Cl2, 2 eq.) is added and the mixture is stirred at rt for 3 h. HOAc (100 μL) is added, the excess DMF is removed in vacuo then the crude product is isolated by extraction with EtOAc from brine. Purification by flash chromatography will give the above titled compound.

Aufarbeitung

  1. customthe excess DMF is removed in vacuo
  2. customthe crude product is isolated by extraction with EtOAc from brine
  3. customPurification by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-aa87b26753454ccd9dca1a0062fa88b5
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05162325

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