Methyl iodide → HCID 69960248, compound

HRID 1291314Notes

Reaction equation

HRID 1291314 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][S:13][C:14]3[N:19]([CH3:20])[C:18]4[NH:21][CH:22]=[CH:23][C:17]=4[C:16](=[O:24])[N:15]=3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:31]I>CS(C)=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:26]=[CH:25][C:11]([CH2:12][S:13][C:14]3[N:19]([CH3:20])[C:18]4[N:21]([CH3:31])[CH:22]=[CH:23][C:17]=4[C:16](=[O:24])[N:15]=3)=[CH:10][CH:9]=2)=[O:7])=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69960974HCID 69960974, compound

Product 1

HCID 69960248HCID 69960248, compoundYield 44.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Under argon gas, 2-[4-(4-chlorobenzoyl) benzyl]thio-1-methyl-7H-pyrrolo(2,3-d]pyrimidin-4-one (103 mg) was dissolved in anhydrous DMSO (20 ml) with warming. Then, at room temperature, 60% sodium hydride-oil (11 mg) was added and the mixture was stirred for 20 minutes. Then, methyl iodide (42.6 mg) was added and the mixture was further stirred overnight. The reaction mixture was diluted with water (200 ml) and the resulting precipitate was collected by filtration, dried, and purified by flash column chromatography (silica gel; chloroform-ethanol: chloroform=1:49) to provide the title compound (47 mg).

Workup

  1. temperaturewith warming
  2. waitthe mixture was further stirred overnight
  3. filtrationthe resulting precipitate was collected by filtration
  4. customdried
  5. custompurified by flash column chromatography (silica gel; chloroform-ethanol: chloroform=1:49)

Sources & evidence

ORD record
ord-0eb7cc7fe72840ff94a7e447a81e8f88
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

Loading…