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

HRID 373125Notes

Reaction equation

HRID 373125 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+].[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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-aa87b26753454ccd9dca1a0062fa88b5
Source dataset
uspto-grants-1992_11
Patent number
US05162325

Reaction notes

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