Lithium Hexamethyldisilazide → 2-Butyl-6-ethenyl-3-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-4(3H)-quinazolinone

HRID 486505Notes

Reaction equation

HRID 486505 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]([CH:16]=[CH2:17])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Br[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[C:42]2[N:46]([C:47]([C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=3)([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[N:45]=[N:44][N:43]=2)=[CH:32][CH:31]=1>O1CCCC1>[CH2:1]([C:5]1[N:14]([CH2:29][C:30]2[CH:31]=[CH:32][C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[C:42]3[N:46]([C:47]([C:60]4[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=4)([C:54]4[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=4)[C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[N:45]=[N:44][N:43]=3)=[CH:34][CH:35]=2)[C:13](=[O:15])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH:16]=[CH2:17])[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 178435592HCID 178435592, compound

Product 1

HCID 152339312-Butyl-6-ethenyl-3-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-4(3H)-quinazolinoneYield 69.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4.49 g of 2-Butyl-6-ethenyl-4(1H)-quinazolinone in 70 ml of dry tetrabydrofuran at room temperature is rapidly added 23.63 9 of a 1.0M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran. After stirring for 20 minutes at room temperature 21.94 g of 5-(4'-(bromomethyl)-[1,1'-biphenyl]-2-yl]-1-(triphenylmethyl)-1H-tetrazole is rapidly added in one portion and the reaction mixture heated at reflux for 48 hours. After cooling to room temperature, the reaction mixture is concentrated in vacuo to a residue which is purified by chromatography on silica gel by eluting with 1:3 ethyl acetate-hexanes to give 9.58 g of the desired product as a yellow solid. FAB MASS SPEC 705 (M+H)

Workup

  1. additionis rapidly added in one portion
  2. temperaturethe reaction mixture heated
  3. temperatureat reflux for 48 hours
  4. concentrationthe reaction mixture is concentrated in vacuo to a residue which
  5. customis purified by chromatography on silica gel
  6. washby eluting with 1:3 ethyl acetate-hexanes

Sources & evidence

ORD record
ord-a995177b1d6a4f8298dedd7767cd5545
Source dataset
uspto-grants-1994_03
Patent number
US05292734

Reaction notes

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