Methyl iodide → HCID 69431059, compound

HRID 854382Notes

Reaction equation

HRID 854382 reaction equation
[CH3:1][O:2][C:3]1[C:4]2[CH:11]=[C:10]([C:12]3[C:20]4[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=4)[NH:14][CH:13]=3)[N:9]([S:23]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[C:5]=2[N:6]=[CH:7][N:8]=1.[H-].[Na+].[CH3:35]I>CN(C)C=O>[CH3:1][O:2][C:3]1[C:4]2[CH:11]=[C:10]([C:12]3[C:20]4[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=4)[N:14]([CH3:35])[CH:13]=3)[N:9]([S:23]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[C:5]=2[N:6]=[CH:7][N:8]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69429466HCID 69429466, compound

Product 1

HCID 69431059HCID 69431059, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-methoxy-6-(5-methoxy-1H-indol-3-yl)-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine [448 mg, Reference Example 5] in dimethylformamide (20 mL) was added the sodium hydride (44 mg, 60% dispersion in oil) and methyl iodide (156 mg) under inert atmosphere. The solution was stirred for 1 hour at room temperature and the solvent was evaporated under reduced pressure. The residue was partitioned between water and ethyl acetate. The organic phase was separated, then dried over magnesium sulfate and then evaporated under reduced pressure. The residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane (30:70, v/v) to give the title compound (260 mg) as an amorphous solid. MS: 464 [MH]+. LCMS (Method B) RT=4.39 minutes.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue was partitioned between water and ethyl acetate
  3. customThe organic phase was separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. additionThe residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane (30:70

Sources & evidence

ORD record
ord-47ecc1e2e3754cb6a1232f69bffa09c6
Source dataset
uspto-grants-2007_08
Patent number
US07259154B2

Reaction notes

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