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

HRID 1677383Notes

Reaction equation

HRID 1677383 reaction equation
[CH3:1][C:2]1([CH:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]4[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=4)[N:17]=3)[NH:12][CH:11]=2)[OH:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[CH3:1][C:2]1([C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]4[CH:20]=[C:21]([O:29][CH3:30])[C:22]([O:27][CH3:28])=[C:23]([O:25][CH3:26])[CH:24]=4)[N:17]=3)[NH:12][CH:11]=2)=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 59540707(1-methyl-cyclohexyl)-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanol

Product 1

HCID 59540565(1-methyl-cyclohexyl)-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanoneYield 22.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1-methyl-cyclohexyl)-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanol (81 mg, 0.196 mmol) in dichloromethane (6 ml) was added Dess-Martin periodinane (125 mg, 0.295 mmol). The reaction mixture was allowed to stir at room temperature for 2 hours. The reaction mixture was partitioned between dichloromethane and 2:1 saturated aqueous NaHCO3:10% aqueous Na2S2O3. The organic layers were collected, dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel chromatography using 20-50% EtOAc in hexanes as eluant to provide 18 mg (22%) of (1-methyl-cyclohexyl)-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone as an off white solid. MP 246-247° C., M+H=439.

Workup

  1. customThe reaction mixture was partitioned between dichloromethane and 2:1 saturated aqueous NaHCO3
  2. customThe organic layers were collected
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-41f372515fcd41008ffb24bafa50f534
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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