Methyl iodide → HCID 57516764, compound

HRID 1894249Notes

Reaction equation

HRID 1894249 reaction equation
[I:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:12][C:11]([CH3:14])([CH3:13])[NH:10][C:9]2=[O:15])=[N:6][CH:7]=1.[H-].[Na+].IC.[C:20]([O-])(O)=O.[Na+]>CN(C=O)C>[I:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:12][C:11]([CH3:13])([CH3:14])[N:10]([CH3:20])[C:9]2=[O:15])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 57516763HCID 57516763, compound

Product 1

HCID 57516764HCID 57516764, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
2.5 °C

Procedure

(55 mg, 173 μmol) 1-(5-Iodo-pyrimidin-2-yl)-4,4-dimethyl-imidazolidin-2-one (Example 122, step 1) was dissolved in DMF (1 ml) and cooled to 0-5° C. NaH (55%) (9 mg, 225 μmol, 1.3 equiv.) was added and the mixture was stirred for 30 min at 0-5° C. Iodomethane (13 μl, 200 μmol, 1.2 equiv.) was added and the mixture was stirred for 30 min without cooling bath. The reaction mixture was treated with sat. NaHCO3 solution and extracted twice with a small volume of CH2Cl2. The organic layers were loaded directly to silica gel column and the crude material was purified by flash chromatography on silica gel (20 gr, ethyl acetate/heptane gradient, 0:100 to 100:0). The desired 1-(5-iodo-pyrimidin-2-yl)-3,4,4-trimethyl-imidazolidin-2-one (31 mg, 54% yield) was obtained as a white solid, MS: m/e=333.1 (M+H+).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. temperaturewithout cooling bath
  3. extractionextracted twice with a small volume of CH2Cl2
  4. customthe crude material was purified by flash chromatography on silica gel (20 gr, ethyl acetate/heptane gradient, 0:100 to 100:0)

Sources & evidence

ORD record
ord-cec7bd90a63141f1b711bfc5abf265d1
Source dataset
uspto-grants-2013_08
Patent number
US08513273B2

Reaction notes

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