Methyl iodide → HCID 18919182, compound

HRID 1291274Notes

Reaction equation

HRID 1291274 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+].[CH3:32]I>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]([CH3:32])[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 6328Methyl iodideHCID 24758Sodium hydrideHCID 1356675827-[4-(4-Chlorobenzoyl)benzyl]-5-methyl-2-methylthio-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one

Product 1

HCID 18919182HCID 18919182, compoundYield 67.1%

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 (254 mg) was dissolved in anhydrous DME (10 ml)-anhydrous DMF (6 ml). Then, 60% sodium hydride-oil (26.4 mg) was added with ice-cooling and, after 30 minutes of agitation, methyl iodide (98 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 then distilled off under reduced pressure and the residue was purified by flash column chromatography (chloroform) to provide the title compound (176 mg). 1H-NMR (CDCl3) δ: 2.39(3H,s), 2.56(3H,s), 3.56(3H,s), 5.29(2H,s), 6.47(1H,d,J=l.OHz), 7.29(2H,d,J=8.4Hz), 7.45(2H,d,J=8.4Hz), 7.73(4H,d,J=8.4Hz).

Workup

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

Sources & evidence

ORD record
ord-c3622eab3ba4413c88c14e4c02da1e5e
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

Loading…