Methyl iodide → HCID 18919017, compound

HRID 1291275Notes

Reaction equation

HRID 1291275 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([C:8]2[CH:26]=[CH:25][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[CH:15]=[CH:14]3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:31]I>COCCOC.C(OCC)(=O)C>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([C:8]2[CH:26]=[CH:25][C:11]([CH2:12][N:13]3[C:17]4[N:18]=[C:19]([S:23][CH3:24])[N:20]([CH3:31])[C:21](=[O:22])[C:16]=4[CH:15]=[CH:14]3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 135667590HCID 135667590, compound

Product 1

HCID 18919017HCID 18919017, compoundYield 35.4%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under argon gas, 7-[4-(4-chlorobenzoyl)benzyl]-2-methylthio-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one (82 mg) was dissolved in anhydrous DME (10 ml)-anhydrous DMF (4 ml). Then, 60% sodium hydride-oil (9.6 mg) was added with ice-cooling and, after 30 minutes of agitation, methyl iodide (34 mg) was added. Then, at room temperature, the mixture was stirred for 2.5 hours. This reaction mixture was diluted with ethyl acetate, washed with saturated aqueous NaCl solution, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by flash column chromatography (hexane: ethyl acetate=4:1) to provide the title compound (30 mg). 1H-NMR (CDCl3) δ: 2.58(3H,s), 3.60(3H,s), 5.37(2H,s), 6.67(1H,d,J=3.4Hz), 6.75(1H,d,J=3.4Hz), 7.30(2H,d,J=8.OHz), 7.45(2H,d,J=8.6Hz), 7.73(2H,d,J=8.6Hz), 7.74(2H,d,J=8.OHz).

Workup

  1. additionwas added
  2. washwashed with saturated aqueous NaCl solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by flash column chromatography (hexane: ethyl acetate=4:1)

Sources & evidence

ORD record
ord-7715390e0d3247faadc45db70ad836e0
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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