Iodoethane → HCID 44200192, compound

HRID 600389Notes

Reaction equation

HRID 600389 reaction equation
[CH3:1][C:2]([CH3:24])([CH3:23])[C:3]([C:5]1[C:13]2[NH:12][C:11](=[O:14])[CH:10]=[N:9][C:8]=2[N:7](COCC[Si](C)(C)C)[CH:6]=1)=[O:4].I[CH2:26][CH3:27].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:26]([O:14][C:11]1[N:12]=[C:13]2[C:5]([C:3](=[O:4])[C:2]([CH3:1])([CH3:23])[CH3:24])=[CH:6][NH:7][C:8]2=[N:9][CH:10]=1)[CH3:27]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 57831039HCID 57831039, compound

Product 1

HCID 44200192HCID 44200192, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 7-(2,2-dimethyl-propionyl)-5-(2-trimethylsilanyl-ethoxymethyl)-1,5-dihydro-pyrrolo[2,3-b]pyrazin-2-one (0.080 g, 0.23 mmol), iodoethane (0.018 mL, 0.24 mmol) and potassium carbonate (0.038 g, 0.28 mmol) in 3 mL of acetone was stirred at reflux overnight, then concentrated. The residue was partitioned between 30 mL of ethyl acetate and 30 mL of water. The organic layer was dried over MgSO4, filtered and concentrated to 0.075 g (86%) of crude 1-[2-ethoxy-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one as a yellow oil that was used without further purification.

Workup

  1. temperatureat reflux overnight
  2. concentrationconcentrated
  3. customThe residue was partitioned between 30 mL of ethyl acetate and 30 mL of water
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to 0.075 g (86%) of crude 1-[2-ethoxy-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one as a yellow oil that
  7. customwas used without further purification

Sources & evidence

ORD record
ord-7b00bd963476481c8c2f5426e5f0590c
Source dataset
uspto-grants-2011_03
Patent number
US07902197B2

Reaction notes

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