Trifluoroacetic acid → 3,3-dimethyl-4-oxo-4-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-butyronitrile

HRID 1677525Notes

Reaction equation

HRID 1677525 reaction equation
[CH3:1][C:2]([CH3:39])([C:6](=[O:38])[C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([C:16]3[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=3)[N:14]=2)[N:9]([Si](C(C)C)(C(C)C)C(C)C)[CH:8]=1)[CH2:3][C:4]#[N:5].FC(F)(F)C(O)=O>ClCCl>[CH3:1][C:2]([CH3:39])([C:6](=[O:38])[C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([C:16]3[CH:17]=[C:18]([O:26][CH3:27])[C:19]([O:24][CH3:25])=[C:20]([O:22][CH3:23])[CH:21]=3)[N:14]=2)[NH:9][CH:8]=1)[CH2:3][C:4]#[N:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 595409513,3-dimethyl-4-oxo-4-[5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-butyronitrile

Product 1

HCID 595410113,3-dimethyl-4-oxo-4-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-butyronitrileYield 9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3,3-dimethyl-4-oxo-4-[5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-butyronitrile (0.093 g, 0.17 mmol) and 0.3 mL of trifluoroacetic acid in 2 mL of dichloromethane was stirred for 15 h, then concentrated. The resulting residue was redissolved in dichloromethane and washed with a sat. aq. NaHCO3 solution, dried over MgSO4, filtered and concentrated to a residue. Column chromatography (0->100% EtOAc/hexanes) afforded 0.006 g (9%) of 3,3-dimethyl-4-oxo-4-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-butyronitrile as a white solid.

Workup

  1. concentrationconcentrated
  2. dissolutionThe resulting residue was redissolved in dichloromethane
  3. washwashed with a sat. aq. NaHCO3 solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to a residue

Sources & evidence

ORD record
ord-5602fb0513774436bde3de5484486365
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

Loading…