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

HRID 1677524Notes

Reaction equation

HRID 1677524 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH:24]([C:31]1[C:39]2[C:34](=[N:35][CH:36]=[C:37]([C:40]3[CH:45]=[C:44]([O:46][CH3:47])[C:43]([O:48][CH3:49])=[C:42]([O:50][CH3:51])[CH:41]=3)[N:38]=2)[N:33]([Si:52]([CH:59]([CH3:61])[CH3:60])([CH:56]([CH3:58])[CH3:57])[CH:53]([CH3:55])[CH3:54])[CH:32]=1)[C:25]([CH3:30])([CH3:29])[CH2:26][C:27]#[N:28]>ClCCl>[CH3:30][C:25]([CH3:29])([C:24](=[O:23])[C:31]1[C:39]2[C:34](=[N:35][CH:36]=[C:37]([C:40]3[CH:45]=[C:44]([O:46][CH3:47])[C:43]([O:48][CH3:49])=[C:42]([O:50][CH3:51])[CH:41]=3)[N:38]=2)[N:33]([Si:52]([CH:56]([CH3:58])[CH3:57])([CH:53]([CH3:54])[CH3:55])[CH:59]([CH3:61])[CH3:60])[CH:32]=1)[CH2:26][C:27]#[N:28]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 595407864-hydroxy-3,3-dimethyl-4-[5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-butyronitrile

Product 1

HCID 595409513,3-dimethyl-4-oxo-4-[5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-butyronitrileYield 61.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

Dess-Martin periodinane (0.122 g, 0.289 mmol) was added to a 0-5° C. solution of 4-hydroxy-3,3-dimethyl-4-[5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-butyronitrile (0.152 g, 0.275 mmol) in 2 mL of dichloromethane. The mixture was stirred at 0-5° C. for 3 h, then quenched with water and a sat. aq. NaHCO3 solution and extracted with 30 mL of dichloromethane. The organic layer was dried over MgSO4, filtered and concentrated to a residue. Column chromatography (0→50% EtOAc/hexanes) afforded 0.093 g (61%) of 3,3-dimethyl-4-oxo-4-[5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-butyronitrile as a white solid.

Workup

  1. customquenched with water
  2. extractiona sat. aq. NaHCO3 solution and extracted with 30 mL of dichloromethane
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to a residue

Sources & evidence

ORD record
ord-397cc17a29fe485090246bb036375ebc
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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