Tetrabutylammonium Fluoride → (1-methyl-cyclopropyl)-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone

HRID 1677391Notes

Reaction equation

HRID 1677391 reaction equation
[CH3:1][C:2]1([C:5]([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[C:13]([C:16]4[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=4)[N:14]=3)[N:9]([Si](C(C)C)(C(C)C)C(C)C)[CH:8]=2)=[O:6])[CH2:4][CH2:3]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][C:2]1([C:5]([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[C:13]([C:16]4[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=4)[N:14]=3)[NH:9][CH:8]=2)=[O:6])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67342981(1-methyl-cyclopropyl)-[5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone

Product 1

HCID 44206485(1-methyl-cyclopropyl)-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanoneYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (1-methyl-cyclopropyl)-[5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone (20 mg, 0.4 mmol) in anhydrous tetrahydrofuran (2 ml) was treated with tetrabutyl ammonium fluoride (1M in tetrahydrofuran, 0.1 ml, 0.1 mmol) dropwise. The reaction mixture was allowed to stir at room temperature for 10 minutes, and then partitioned between EtOAc/water. The organic layers were collected, dried over MgSO4, filtered, and concentrated giving a yellow solid. The residue was purified by preparative thin layer chromatography using 70% EtOAc in hexanes as eluant to provide 10 mg (71%) of (1-methyl-cyclopropyl)-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone as a white solid. M+H=368.

Workup

  1. custompartitioned between EtOAc/water
  2. customThe organic layers were collected
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customgiving a yellow solid
  7. customThe residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-1308c7d92bde4a39a19563aad6402c27
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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