Ethyl Acetate → HCID 135804112, compound

HRID 2415025Notes

Reaction equation

HRID 2415025 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[NH:12][C:11](=[O:13])[CH:10]=[C:9]([C:14]([F:17])([F:16])[F:15])[N:8]=1.C(OCC)(=O)C.[I:24]N1C(=O)CCC1=O>>[I:24][C:10]1[C:11](=[O:13])[NH:12][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[N:8][C:9]=1[C:14]([F:16])([F:17])[F:15]

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 120273N-IodosuccinimideHCID 1354099312-(Pyridin-2-yl)-6-(trifluoromethyl)pyrimidin-4(1H)-one

Product 1

HCID 135804112HCID 135804112, compound

Conditions

Temperature
132.5 °C

Procedure

2-(Pyridin-2-yl)-6-trifluoromethyl-3H-pyrimidin-4-one (15.0 g) was dissolved in DMP (150 ml) and N-iodosuccinimide (33.6 g) was added at room temperature with stirring. The mixture was stirred under heating (130-135° C.) for 6 hr. and then cooled to room temperature. The reaction mixture was added ethyl acetate (150 ml), and then washed with aqueous sodium thiosulfate, water and brine, respectively. The ethyl acetate layer was dried over magnesium sulfate and the solvent was removed under reduced pressure to give crude 5-iodo-2-(pyridine-2-yl)-6-trifluoromethyl-3H-pyrimidin-4-one. It was recrystallized from toluene as pale brown needles (10.2 g), mp 186-187° C.

Workup

  1. additionwas added at room temperature
  2. stirringThe mixture was stirred
  3. temperatureand then cooled to room temperature
  4. washwashed with aqueous sodium thiosulfate, water and brine
  5. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3228fa5ac46f42efb310dbbd9c23d0fe
Source dataset
uspto-grants-2004_11
Patent number
US06818631B1

Reaction notes

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