Methyl iodide → 3,5-Dimethyl-7-[4-(4-fluorobenzoyl)benzyl]-2-methylthio-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one

HRID 1291307Notes

Reaction equation

HRID 1291307 reaction equation
[F: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+].[CH3:32]I>COCCOC.C(OCC)(=O)C>[CH3:32][N:20]1[C:21](=[O:22])[C:16]2[C:15]([CH3:25])=[CH:14][N:13]([CH2:12][C:11]3[CH:26]=[CH:27][C:8]([C:6](=[O:7])[C:5]4[CH:28]=[CH:29][C:2]([F:1])=[CH:3][CH:4]=4)=[CH:9][CH:10]=3)[C:17]=2[N:18]=[C:19]1[S:23][CH3:24]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1356675887-[4-(4-Fluorobenzoyl)benzyl]-5-methyl-2-methylthio-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one

Product 1

HCID 189190113,5-Dimethyl-7-[4-(4-fluorobenzoyl)benzyl]-2-methylthio-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-oneYield 68.5%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under argon gas, 7-[4-(4-fluorobenzoyl)benzyl]-5-methyl-2-methylthio-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one (1.85 g) was dissolved in anhydrous DME (50 ml)anhydrous DMF (50 ml) and, under ice-cooling, 60% sodium hydride-oil (176 mg) was added in two installments. After 30 minutes of stirring, methyl iodide (681 mg) was added. Then, at room temperature, the mixture was stirred overnight. This 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; ethyl acetate: hexane=1:5.6-1:2.3) to provide the title compound (1.31 g).

Workup

  1. temperaturecooling
  2. stirringThen, at room temperature, the mixture was stirred overnight
  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; ethyl acetate: hexane=1:5.6-1:2.3)

Sources & evidence

ORD record
ord-0852f65e55594c3ba61a3d3b95ce4df7
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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