Potassium Carbonate → 4'-[[2-Butyl-4-oxo-6-[2-(4-pentenyl)-2H-tetrazol-5-yl]-3(4H)-quinazolinyl]methyl]-[1,1'-biphenyl]2-carbonitrile

HRID 486624Notes

Reaction equation

HRID 486624 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]1[N:17]=[N:18][N:19]([CH2:21][CH2:22][CH2:23][CH:24]=[CH2:25])[N:20]=1)=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4].Br[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[C:35]([C:40]#[N:41])=[CH:36][CH:37]=[CH:38][CH:39]=2)=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([C:5]1[N:14]([CH2:27][C:28]2[CH:29]=[CH:30][C:31]([C:34]3[C:35]([C:40]#[N:41])=[CH:36][CH:37]=[CH:38][CH:39]=3)=[CH:32][CH:33]=2)[C:13](=[O:15])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:16]3[N:17]=[N:18][N:19]([CH2:21][CH2:22][CH2:23][CH:24]=[CH2:25])[N:20]=3)[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15019124'-(Bromomethyl)-2-cyanobiphenylHCID 178446235HCID 178446235, compound

Product 1

HCID 190958484'-[[2-Butyl-4-oxo-6-[2-(4-pentenyl)-2H-tetrazol-5-yl]-3(4H)-quinazolinyl]methyl]-[1,1'-biphenyl]2-carbonitrileYield 94.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1.01 g of 2-butyl-6-[2-(4-pentenyl)-2H-tetrazol-5-yl]-4(1H)-quinazolinone, 1.09 g of 4'-(bromomethyl)[1,1'-biphenyl]-2-carbonitrile and 2.0 g of potassium carbonate in 100 ml of acetone is refluxed for 24 hours. The reaction mixture is filtered and the filtrate evaporated in vacuo to a residue which is purified by chromatography on silica gel by elution with 30% ethyl acetate-hexanes to give 1.5 g of the desired product as a yellow foam.

Workup

  1. temperatureis refluxed for 24 hours
  2. filtrationThe reaction mixture is filtered
  3. customthe filtrate evaporated in vacuo to a residue which
  4. customis purified by chromatography on silica gel by elution with 30% ethyl acetate-hexanes

Sources & evidence

ORD record
ord-171183c2c77b4b3fba4b4d9edc55010d
Source dataset
uspto-grants-1994_03
Patent number
US05292742

Reaction notes

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