Dichloromethane → HCID 59540679, compound

HRID 1677533Notes

Reaction equation

HRID 1677533 reaction equation
[CH3:1][C:2]([CH3:39])([CH3:38])[C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([C:14]3[CH:19]=[C:18]([N:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)[CH:17]=[C:16]([O:25][CH2:26][CH2:27]SC)[CH:15]=3)[N:12]=2)[N:7]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[CH:6]=1)=[O:4].[S:40](=[O:43])(O)[O-:41].[Na+].[CH2:45](Cl)Cl>O.CC(C)=O.O=[Os](=O)(=O)=O>[CH3:45][S:40]([CH2:27][CH2:26][O:25][C:16]1[CH:15]=[C:14]([C:11]2[N:12]=[C:13]3[C:5]([C:3](=[O:4])[C:2]([CH3:1])([CH3:39])[CH3:38])=[CH:6][N:7]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:35])[CH3:36])[C:8]3=[N:9][CH:10]=2)[CH:19]=[C:18]([N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[CH:17]=1)(=[O:43])=[O:41]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 23665763Sodium BisulfiteHCID 59540949HCID 59540949, compound

Product 1

HCID 59540679HCID 59540679, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

To a solution of 2,2-dimethyl-1-[2-[3-(2-methylsulfanyl-ethoxy)-5-pyrrolidin-1-yl-phenyl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one (82 mg, 0.14 mmol) in 20% water/acetone (3 ml) was added 4-methylmorpholine n-oxide (50 mg, 0.43 mmol) followed by addition of aqueous OsO4 solution (0.01 ml, catalytic). After 8 hours stirring a solution of 5% aqueous sodium bisulfite (25 ml) was added followed by CH2Cl2 (25 ml). The material was partitioned and the organic phase collected and then washed with brine (25 ml). The aqueous phases were back-extracted with methylene chloride (2×25 ml), the organic phases combined, dried (MgSO4), filtered and stripped to provide a crude remainder. The material was loaded onto 1 preparative TLC plate, eluting with 40% ethyl acetate in hexanes. The product band was collected to afford 75 mg of 1-[2-[3-(2-methanesulfonyl-ethoxy)-5-pyrrolidin-1-yl-phenyl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one as a yellow viscous oil.

Workup

  1. additionwas added
  2. customThe material was partitioned
  3. customthe organic phase collected
  4. washwashed with brine (25 ml)
  5. extractionThe aqueous phases were back-extracted with methylene chloride (2×25 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customto provide a crude remainder
  9. washeluting with 40% ethyl acetate in hexanes
  10. customThe product band was collected

Sources & evidence

ORD record
ord-4588e613e77c449295ab985818c28f65
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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