Potassium Carbonate → 3-[(4-Bromophenyl)methyl]-2-butyl-6-(1-hydroxy-1-methylethyl)-4(3H)-quinazolinone

HRID 1654150Notes

Reaction equation

HRID 1654150 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]([C:16]([OH:19])([CH3:18])[CH3:17])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4].[Br:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][N:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([C:16]([OH:19])([CH3:18])[CH3:17])[CH:11]=3)[N:6]=[C:5]2[CH2:1][CH2:2][CH2:3][CH3:4])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 685274-Bromobenzyl bromideHCID 178441842HCID 178441842, compound

Product 1

HCID 200793443-[(4-Bromophenyl)methyl]-2-butyl-6-(1-hydroxy-1-methylethyl)-4(3H)-quinazolinone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1.37 g of 2-butyl-6-(1-hydroxy-1-methylethyl)-4(1H)-quinazolinone in 115 ml of acetone is added 1.58 g of 4-bromobenzyl bromide and 2.18 g of anhydrous potassium carbonate. The resulting suspension is heated to reflux for 16 hours. The reaction mixture is then allowed to cool to room temperature, filtered and the filtrate is concentrated in vacuo. The residue is purified by HPLC eluting with ethyl acetate/hexanes (1:3) to provide the desired product.

Workup

  1. temperatureThe resulting suspension is heated
  2. temperatureto reflux for 16 hours
  3. filtrationfiltered
  4. concentrationthe filtrate is concentrated in vacuo
  5. customThe residue is purified by HPLC
  6. washeluting with ethyl acetate/hexanes (1:3)

Sources & evidence

ORD record
ord-333bf914d0a54beca6accc3ba7812c53
Source dataset
uspto-grants-1995_04
Patent number
US05405849

Reaction notes

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