Methyl iodide → HCID 18919080, compound

HRID 1291281Notes

Reaction equation

HRID 1291281 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([C:8]2[CH:9]=[C:10]([CH:24]=[CH:25][CH:26]=2)[CH2:11][S:12][C:13]2[NH:14][C:15](=O)C3[C:21]([CH3:22])=[CH:20][NH:19][C:17]=3[N:18]=2)=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:31]I.CO[CH2:35][CH2:36][O:37]C>C(OCC)(=O)C>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([C:8]2[CH:9]=[C:10]([CH:24]=[CH:25][CH:26]=2)[CH2:11][S:12][C:13]2[N:14]([CH3:15])[C:36](=[O:37])[C:35]3[C:21]([CH3:22])=[CH:20][N:19]([CH3:31])[C:17]=3[N:18]=2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 80711,2-DimethoxyethaneHCID 24758Sodium hydrideHCID 135667586HCID 135667586, compound

Product 1

HCID 18919080HCID 18919080, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Under argon gas, 2-[3-(4-chlorobenzoyl) benzyl]thio-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one (1.31 g) was suspended in anhydrous DME (32 ml) and, under ice-cooling and stirring, 60% sodium hydride-oil (269 mg) was added in two installments. The mixture was stirred for 15 minutes, after which methyl iodide (1.18 g) was added. Then, the mixture was further stirred at room temperature 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 (hexane: ethyl acetate=4:1-2.5:1) to provide the title compound (950 mg). 1H-NMR (CDCl3) δ: 2.39(3H,d,J=1.0 Hz), 3.53(3H,s), 3.54(3H,s), 4.52(2H,s), 6.42(1H,d,J=1.0 Hz), 7.36(2H,d,J=8.6 Hz), 7.35-7.50(1H,m), 7.65-7.72(2H,m), 7.69(2H,d,J=8.6 Hz), 7.97(1H,d,J=1.6 Hz).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 15 minutes
  3. stirringThen, the mixture was further stirred at room temperature overnight
  4. washwashed with saturated aqueous NaCl solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was then distilled off under reduced pressure
  7. customthe residue was purified by flash column chromatography (hexane: ethyl acetate=4:1-2.5:1)

Sources & evidence

ORD record
ord-98788adfc98c49c5a2d43d1455ec769c
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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