N-Iodosuccinimide → 5-Iodo-6-(trifluoromethyl)pyrimidin-4(3H)-one

HRID 1886142Notes

Reaction equation

HRID 1886142 reaction equation
[I:1]N1C(=O)CCC1=O.[F:9][C:10]([F:19])([F:18])[C:11]1[N:12]=[CH:13][NH:14][C:15](=[O:17])[CH:16]=1>C(#N)C>[I:1][C:16]1[C:15](=[O:17])[NH:14][CH:13]=[N:12][C:11]=1[C:10]([F:9])([F:18])[F:19]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 1354586204-Hydroxy-6-(trifluoromethyl)pyrimidine

Product 1

HCID 1360663385-Iodo-6-(trifluoromethyl)pyrimidin-4(3H)-oneYield 8.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Iodosuccinimide (2.75 g) was added to a stirred suspension of 4-trifluoromethylpyrimidin-6-one (1 g) in dry acetonitril (13 ml). The reaction mixture was stirred at the ambient temperature for 2 hours, and then heated under reflux for 10 hours. After cooling, removal of the solvent under reduced pressure gave a brown solid which was recrystallised from water to give 5-iodo-4-trifluoromethylpyrimidin-6-one as a pale orange solid (150 mg);

Workup

  1. temperatureheated
  2. temperatureunder reflux for 10 hours
  3. temperatureAfter cooling
  4. customremoval of the solvent under reduced pressure
  5. customgave a brown solid which
  6. customwas recrystallised from water

Sources & evidence

ORD record
ord-8dabd6c5e4a8483d9ec805f25bc45a6e
Source dataset
uspto-grants-1992_09
Patent number
US05149810

Reaction notes

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