Water → HCID 59540546, compound

HRID 1677386Notes

Reaction equation

HRID 1677386 reaction equation
[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: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)=[O:9])[CH2:7][CH2:6]S[CH2:4][CH2:3]1.O.O[O:33][S:34]([O-:36])=O.[K+]>C(#N)C.CO>[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])[CH2:7][CH2:6][S:34](=[O:36])(=[O:33])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 49764440HCID 49764440, compound

Product 1

HCID 59540546HCID 59540546, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A suspension of (4-methyl-tetrahydro-thiopyran-4-yl)-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone (9 mg, 0.02 mmol) in acetonitrile (0.4 ml), MeOH (0.4 ml), and water (0.2 ml) was treated with Oxone (26 mg, 0.04 mmol) and stirred overnight at room temperature. The reaction mixture was partitioned between EtOAc/water. The organic layers were collected, dried over Na2SO4, filtered, and concentrated. The residue was purified by preparative thin layer chromatography using 30% EtOAc in hexanes as eluant to provide 6 mg (62%) of (4-methyl-1,1-dioxo-hexahydro-1lambda*6*-thiopyran-4-yl)-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone as an off white solid. M+H=460.

Workup

  1. customThe reaction mixture was partitioned between EtOAc/water
  2. customThe organic layers were collected
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-0b4847bec86d4a7796dddef8a197fbee
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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