Tetrabutylammonium Fluoride → HCID 59678643, compound

HRID 1751884Notes

Reaction equation

HRID 1751884 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][O:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[C:16](OS(C(F)(F)F)(=O)=O)[N:15]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[F-:32].C([N+](CCCC)(CCCC)CCCC)CCC>O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][O:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[C:16]([F:32])[N:15]=2)=[CH:7][CH:6]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59678702HCID 59678702, compound

Product 1

HCID 59678643HCID 59678643, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 15 ml round bottom flask is charged with 4-(2-(4-tert-butylphenyl)-ethoxy)-2-(trifluoromethanesulfonyloxy)-quinazoline (0.3 g, 0.66 mmol). Tetrabutylammonium fluoride solution (1M in THF, 3.3 ml, 3.3 mmol) is then added to it and the solution refluxed for 60 minutes. The mixture is then cooled and water is added to it. It is then extracted with dichloromethane, washed with water and dried. The crude obtained after concentration is purified by silica gel flash chromatography (ethyl acetate/hexanes) to obtain the desired compound.

Workup

  1. temperaturethe solution refluxed for 60 minutes
  2. temperatureThe mixture is then cooled
  3. extractionIt is then extracted with dichloromethane
  4. washwashed with water
  5. customdried
  6. customThe crude obtained
  7. concentrationafter concentration
  8. customis purified by silica gel flash chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-656a18b72ab148668bb7079f93e85071
Source dataset
uspto-grants-2015_10
Patent number
US09161997B2

Reaction notes

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