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

HRID 1926133Notes

Reaction equation

HRID 1926133 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 was 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 was 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-dacc69e5c2084dc7a9664fed5adcfcd7
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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