Methyl iodide → HCID 67998151, compound

HRID 1425983Notes

Reaction equation

HRID 1425983 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[N:6][C:7]([N:10]2[CH2:14][CH2:13][NH:12][C:11]2=[O:15])=[N:8][CH:9]=1.[CH3:16]I>CN(C)C=O>[Br:3][C:4]1[CH:5]=[N:6][C:7]([N:10]2[CH2:14][CH2:13][N:12]([CH3:16])[C:11]2=[O:15])=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67997610HCID 67997610, compound

Product 1

HCID 67998151HCID 67998151, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (10 mg) was added to a solution of 1-(5-bromopyrimidin-2-yl)imidazolidin-2-one (50 mg) in N,N-dimethylformamide (5 mL) under nitrogen at 0° C. After stirring for 30 min, MeI (36 mg) was added. The reaction mixture was stirred at room temperature until the starting material was completely consumed (TLC). The reaction mixture was then quenched with H2O (20 mL) and the resulting mixture was extracted with ethyl acetate (3×20 mL). The combined extracts were washed with H2O (3×20 mL), dried (Na2SO4), and concentrated. The residue was purified by preparative TLC to afford the title compound. Yield: 10 mg (19% of theory).

Workup

  1. stirringThe reaction mixture was stirred at room temperature until the starting material
  2. customwas completely consumed (TLC)
  3. customThe reaction mixture was then quenched with H2O (20 mL)
  4. extractionthe resulting mixture was extracted with ethyl acetate (3×20 mL)
  5. washThe combined extracts were washed with H2O (3×20 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-90ff4c4812b84e01b213bfc523d5fc99
Source dataset
uspto-grants-2015_01
Patent number
US08933072B2

Reaction notes

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