Methyl iodide → HCID 18342785, compound

HRID 2300854Notes

Reaction equation

HRID 2300854 reaction equation
[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([N:25]5[CH2:29][CH2:28][NH:27][C:26]5=[O:30])=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].I[CH3:34]>CN(C=O)C>[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([N:25]5[CH2:29][CH2:28][N:27]([CH3:34])[C:26]5=[O:30])=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18342791HCID 18342791, compound

Product 1

HCID 18342785HCID 18342785, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[(S)-1-Phenylethylamino]-4-[5-(imidazolidin-2-on-1-yl)benzimidazol-1-yl]pyrimidine (Example 385) (0.025 mmol) in anhydrous DMF (0.2 ml) under nitrogen was added NaH (60%) in one portion. After stirring for ten minutes, iodomethane (0.028 mmol) was added dropwise. The reaction was stirred at room temperature for 2.5 h. and quenched with water. The mixture was extracted with methylene chloride. The organic extracts were combined, washed with brine and dried over MgSO4. Removal of the solvent and subsequent purification by preparative thin layer chromatography (acetone/hexane system) provided 4.5 mg of the title compound. Mass spectrum (ESI) 414.3 (M+1).

Workup

  1. stirringThe reaction was stirred at room temperature for 2.5 h.
  2. customquenched with water
  3. extractionThe mixture was extracted with methylene chloride
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. customRemoval of the solvent and subsequent purification by preparative thin layer chromatography (acetone/hexane system)

Sources & evidence

ORD record
ord-f415f419bf494ce8ba6a12375bf23b52
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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