Potassium Carbonate → 6-Acetyl-2-butyl-3-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-4(3H)-quinazolinone

HRID 486501Notes

Reaction equation

HRID 486501 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([CH2:14][CH2:15][CH2:16][CH3:17])=[N:8][C:7]2=[O:18])(=[O:3])[CH3:2].Br[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]2[N:37]([C:38]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[N:36]=[N:35][N:34]=2)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([CH2:14][CH2:15][CH2:16][CH3:17])[N:8]([CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]3[N:37]([C:38]([C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)([C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=4)[C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[N:36]=[N:35][N:34]=3)=[CH:25][CH:26]=1)[C:7]2=[O:18])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 178441846HCID 178441846, compound

Product 1

HCID 152339306-Acetyl-2-butyl-3-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-4(3H)-quinazolinoneYield 58.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 0.250 g of 6-acetyl-2-butyl-4(1H)-quinazolinone, 0.685 g of 5-[4'-(bromomethyl)-[1,1'-biphenyl]-2-yl]-1-(triphenylmethyl) -1H-tetrazole and 0.424 g of anhydrous potassium carbonate in 25.0 ml of dry acetone is heated at reflux for 16 hours. The reaction mixture is alowed to cool to room temperature, filtered and the filtrate evaporated in vacuo to a residue. The residue is purified by column chromatography on silica gel using 1:3 ethyl acetate-hexanes to give 0.43 g of the desired product as a solid, m.p. 104°-105° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 16 hours
  3. filtrationfiltered
  4. customthe filtrate evaporated in vacuo to a residue
  5. customThe residue is purified by column chromatography on silica gel using 1:3 ethyl acetate-hexanes

Sources & evidence

ORD record
ord-a14fcf3c608d42cd98a9614f79b5ab57
Source dataset
uspto-grants-1994_03
Patent number
US05292734

Reaction notes

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