Iodoethane → HCID 18918993, compound

HRID 1291305Notes

Reaction equation

HRID 1291305 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([C:8]2[CH:27]=[CH:26][C:11]([CH2:12][N:13]3[C:17]4[N:18]=[C:19]([S:23][CH3:24])[NH:20][C:21](=[O:22])[C:16]=4[C:15]([CH3:25])=[CH:14]3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:32](I)[CH3:33]>COCCOC.C(OCC)(=O)C>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([C:8]2[CH:27]=[CH:26][C:11]([CH2:12][N:13]3[C:17]4[N:18]=[C:19]([S:23][CH3:24])[N:20]([CH2:32][CH3:33])[C:21](=[O:22])[C:16]=4[C:15]([CH3:25])=[CH:14]3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 1356675827-[4-(4-Chlorobenzoyl)benzyl]-5-methyl-2-methylthio-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one

Product 1

HCID 18918993HCID 18918993, compoundYield 39.7%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under argon gas, 7-[4-(4-chlorobenzoyl)benzyl]-5-methyl-2-methylthio-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one (2.46 g) was dissolved in anhydrous DME (72.5 ml)anhydrous DMF (72.5 ml) and, under ice-cooling, 60% sodium hydride-oil (255 mg) was added in two installments. The mixture was stirred for 30 minutes sand ethyl iodide (1.09 g) was added. Then, the mixture was further stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous NaCl solution, and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure and the residue was purified by flash column chromatography [silica gel; dichloromethane→methanol: dichloromethane (1:49)] to provide the title compound (1.04 g).

Workup

  1. temperaturecooling
  2. additionwas added
  3. washwashed with saturated aqueous NaCl solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was then distilled off under reduced pressure
  6. customthe residue was purified by flash column chromatography [silica gel; dichloromethane→methanol: dichloromethane (1:49)]

Sources & evidence

ORD record
ord-bf0868ad5f914e26a9190a60b633bf9a
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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