Methyl Methanesulfonate → 4,6-diiodo-N-methylpyrimidin-5-amine

HRID 1787047Notes

Reaction equation

HRID 1787047 reaction equation
[I:1][C:2]1[C:7]([NH2:8])=[C:6]([I:9])[N:5]=[CH:4][N:3]=1.[H-].[Na+].[CH3:12]S(OC)(=O)=O.C(OCC)(=O)C>O1CCCC1>[I:1][C:2]1[C:7]([NH:8][CH3:12])=[C:6]([I:9])[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 4156Methyl MethanesulfonateHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 118101544,6-Diiodopyrimidin-5-amine

Product 1

HCID 251863624,6-diiodo-N-methylpyrimidin-5-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4,6-diiodopyrimidin-5-amine (1.0 g) in tetrahydrofuran (10 mL) was added sodium hydride (60%, 138 mg) under ice-cooling. The mixture was stirred at room temperature for 30 min. To the reaction system was added dropwise a solution of methyl methanesulfonate (0.256 mL) in tetrahydrofuran (4.0 mL). The mixture was stirred at room temperature for 3 hrs and ethyl acetate was added. The mixture washed with water and saturated brine and dried over magnesium sulfate. After concentration under reduced pressure, the residue was separated and purified by silica gel column chromatography (hexane:ethyl acetate=9:1→3:1) to give the title compound (600 mg) as pale-yellow crystals.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 3 hrs
  3. washThe mixture washed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationAfter concentration under reduced pressure
  6. customthe residue was separated
  7. custompurified by silica gel column chromatography (hexane:ethyl acetate=9:1→3:1)

Sources & evidence

ORD record
ord-72c172c741374100bf28532885c01fb5
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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