Tetrabutylammonium Fluoride → HCID 44192425, compound

HRID 1677410Notes

Reaction equation

HRID 1677410 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][N:2]1[C:10]1[N:11]=[C:12]2[C:18]([C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:17][N:16](COCC[Si](C)(C)C)[C:13]2=[N:14][CH:15]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][N:2]1[C:10]1[N:11]=[C:12]2[C:18]([C:19](=[O:24])[C:20]([CH3:22])([CH3:21])[CH3:23])=[CH:17][NH:16][C:13]2=[N:14][CH:15]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67202278HCID 67202278, compound

Product 1

HCID 44192425HCID 44192425, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
85 °C

Procedure

To a solution of 1-[2-(1,3-Dihydro-isoindol-2-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (270 mg, 0.599 mmol) in 7 mL of THF was added 5.99 mL (5.99 mmol) of 1.0 M TBAF in THF. Heated the mixture to 85° C. for 2 h. The reaction was quenched with 5 mL acetone and 15 mL of saturated aqueous NaHCO3 then diluted with ethyl acetate and water and partitioned. The organic phase was washed with brine, dried over MgSO4, filtered, and concentrated. Recrystallization from dichloromethane afforded 153.3 mg (80% yield) of 1-[2-(1,3-Dihydro-isoindol-2-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one as a white solid.

Workup

  1. customThe reaction was quenched with 5 mL acetone and 15 mL of saturated aqueous NaHCO3
  2. additionthen diluted with ethyl acetate and water
  3. custompartitioned
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customRecrystallization from dichloromethane

Sources & evidence

ORD record
ord-fd82800932c049bfa6d9f86439631e5b
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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