Tetrabutylammonium Fluoride → HCID 67521035, compound

HRID 1924422Notes

Reaction equation

HRID 1924422 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[N:11]([NH:22][C:23](=[O:33])[CH2:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[C:27]([F:32])[CH:26]=1)[C:10]2=[O:34])(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:20]([N:17]([CH2:18][CH3:19])[C:12]1[N:11]([NH:22][C:23](=[O:33])[CH2:24][C:25]2[CH:30]=[C:29]([F:31])[CH:28]=[C:27]([F:32])[CH:26]=2)[C:10](=[O:34])[C:9]2[C:14](=[CH:15][CH:16]=[C:7]([OH:6])[CH:8]=2)[N:13]=1)[CH3:21]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67521366HCID 67521366, compound

Product 1

HCID 67521035HCID 67521035, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-[6-(tert-Butyl-dimethyl-silanyloxy)-2-diethylamino-4-oxo-4H-quinazolin-3-yl]-2-(3,5-difluoro-phenyl)-acetamide (1.50 g, 2.85 mmol) was dissolved in dry THF (50 mL). Tetrabutylammonium fluoride (1 M in THF, 3.13 mL, 3.13 mmol) was added to the mixture over 10 minutes at RT. Stirring was continued for 30 minutes. The solvent was removed in vacuo and the residue was subjected to column chromatography (EtOAc/Heptane) giving the title compound (0.60 g, 54%).

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ccdfc42e36714bf792c3bfb3935763d6
Source dataset
uspto-grants-2012_05
Patent number
US08178544B2

Reaction notes

Loading…