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

HRID 373129Notes

Reaction equation

HRID 373129 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-58dae8270e5940adaf96ffe1afb7a2b3
Source dataset
uspto-grants-1992_11
Patent number
US05162325

Reaction notes

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