Tetrabutylammonium Fluoride → 3-(4-sec-butylphenyl)-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one

HRID 1846262Notes

Reaction equation

HRID 1846262 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][CH2:28][O:29][C:30]1[C:35]([CH3:36])=[CH:34][C:33]([C:37]2[N:46]([C:47]3[CH:52]=[CH:51][C:50]([CH:53]([CH2:55][CH3:56])[CH3:54])=[CH:49][CH:48]=3)[C:45](=[O:57])[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[N:38]=2)=[CH:32][C:31]=1[CH3:58])(C(C)(C)C)(C)C>C1COCC1>[CH:53]([C:50]1[CH:49]=[CH:48][C:47]([N:46]2[C:45](=[O:57])[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[N:38]=[C:37]2[C:33]2[CH:32]=[C:31]([CH3:58])[C:30]([O:29][CH2:28][CH2:27][OH:26])=[C:35]([CH3:36])[CH:34]=2)=[CH:52][CH:51]=1)([CH2:55][CH3:56])[CH3:54]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 585325112-(4-(2-(tert-butyldimethylsilyloxy)ethoxy)-3,5-dimethylphenyl)-3-(4-sec-butylphenyl)quinazolin-4(3H)-one

Product 1

HCID 467007623-(4-sec-butylphenyl)-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1 M solution of tetrabutyl ammonium fluoride in THF was added to a solution of 2-(4-(2-(tert-butyldimethylsilyloxy)ethoxy)-3,5-dimethylphenyl)-3-(4-sec-butylphenyl)quinazolin-4(3H)-one in THF at 0° C. The ice bath was removed, and stirring was continued at room temperature for 2 hours. The solvent was evaporated, and residue was taken in dichloromethane, concentrated and purified as described in Example 1 to give the title compound.

Workup

  1. customThe ice bath was removed
  2. customThe solvent was evaporated
  3. concentrationconcentrated
  4. custompurified

Sources & evidence

ORD record
ord-f3a13d8ca0e34a5f93a30fe911706fbf
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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