Tetrabutylammonium Fluoride → HCID 57829629, compound

HRID 1677508Notes

Reaction equation

HRID 1677508 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]3[C:16]([C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:15][N:14](COCC[Si](C)(C)C)[C:11]3=[N:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C(OCC)(=O)C>[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]3[C:16]([C:17](=[O:22])[C:18]([CH3:20])([CH3:19])[CH3:21])=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57829644HCID 57829644, compound

Product 1

HCID 57829629HCID 57829629, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a microwave vial was added 0.032 gm (0.075 mM) 1-[2-(3-Amino-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one followed by 0.75 ml of 1M tetrabutylammonium fluoride in THF. The vial was sealed and placed in a 80° C. oil bath for two hours then stirred at room temperature overnight. The mixture was diluted with 10 ml ethyl acetate, rinsed (3×50 ml) water, dried over magnesium sulfate, filtered and concentrated on a rotary evaporator. Purification on a preparative silica gel thin layer chromatography plate (5/95 MeOH/CH2Cl2) gave 0.014 gm (64% yield) of 1-[2-(3-Amino-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one, M+1 295, M.P. 239-241° C.

Workup

  1. customThe vial was sealed
  2. customplaced in a 80° C.
  3. customfor two hours
  4. washrinsed (3×50 ml) water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated on a rotary evaporator
  8. customPurification on a preparative silica gel thin layer chromatography plate (5/95 MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-00607d1ad1b446e9a119474adf482206
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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