N-Iodosuccinimide → HCID 57930763, compound

HRID 1893918Notes

Reaction equation

HRID 1893918 reaction equation
[CH2:1]([NH:3][C:4]1[N:9]=[C:8]([NH:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:7]=[C:6]([CH3:17])[N:5]=1)[CH3:2].[I:18]N1C(=O)CCC1=O>CC#N>[CH2:1]([NH:3][C:4]1[N:9]=[C:8]([NH:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:7]([I:18])=[C:6]([CH3:17])[N:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 57930764HCID 57930764, compound

Product 1

HCID 57930763HCID 57930763, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-ethylamino-4-cyclohexylamino-6-methylpyrimidine (600 mg, 2.56 mmol) in CH3CN (10 mL) was added N-iodosuccinimide (NIS, 658 mg, 2.92 mmol). The reaction was stirred for 2 h at room temperature. After removal of the solvent, the residue was dissolved in EtOAc. The organic phase was then washed with sodium bisulfite, brine, and dried over Na2SO4. Purification by flash column chromatography gave 660 mg (73% yield) of 2-ethylamino-4-cyclohexylamino-5-iodo-6-methylpyrimidine.

Workup

  1. customAfter removal of the solvent
  2. dissolutionthe residue was dissolved in EtOAc
  3. washThe organic phase was then washed with sodium bisulfite, brine
  4. dry with materialdried over Na2SO4
  5. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-d8e0f28fe9c64156a86f61798ca7de9d
Source dataset
uspto-grants-2013_08
Patent number
US08513266B2

Reaction notes

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