N-Iodosuccinimide → 2-Amino-5-iodo-3-methyl-6-phenylpyrimidin-4(3H)-one

HRID 1981586Notes

Reaction equation

HRID 1981586 reaction equation
[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:3]=1.[I:16]N1C(=O)CCC1=O>C(O)(=O)C>[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[C:5]([I:16])=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:3]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 133205052-Amino-3-methyl-6-phenyl-4-pyrimidinone

Product 1

HCID 133205062-Amino-5-iodo-3-methyl-6-phenylpyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 1.8 g (8.95 mM) of 2-amino-3-methyl-6-phenyl-4-pyrimidinone was added 75 ml glacial acetic acid and 1.98 g N-iodosuccinimide (8.8 mM). The reaction mixture was heated to 70° for 5 hours. The mixture was allowed to cool to room temperature and evaporated to dryness under vacuum. The residual solid was azeotroped twice from absolute EtOH, heated to reflux with 50 ml absolute EtOH and allowed to cool to room temperature. The solids were filtered, washed well with absolute EtOH, and dried at 80° for 18 hours. Yield of yellow crystals was 1.6 g (56%).

Workup

  1. temperatureThe reaction mixture was heated to 70° for 5 hours
  2. customevaporated to dryness under vacuum
  3. customThe residual solid was azeotroped twice from absolute EtOH
  4. temperatureheated
  5. temperatureto reflux with 50 ml absolute EtOH
  6. temperatureto cool to room temperature
  7. filtrationThe solids were filtered
  8. washwashed well with absolute EtOH
  9. customdried at 80° for 18 hours

Sources & evidence

ORD record
ord-3559575e05464b0f8045ce4d32b5b50a
Source dataset
uspto-grants-1986_06
Patent number
US04593096

Reaction notes

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