Iodine → HCID 90197331, compound

Temperature

80 °C

To a suspension of 1-(3-(trifluoromethyl)phenyl)pyrimidin-2,4(1H,3H)-dione (prepared in Reference Example 113) (5.09 g) in acetonitrile (75 ml) were added iodine (3.03 g) and cerium ammonium nitrate (6.54 g) and the resulting mixture was stirred at 80° C. for thirty minutes. The resulting mixture was cooled to 0° C. and thereto were then added ethyl acetate (150 ml), saturated saline (50 ml) and 5% sodium hydrogen sulfite solution (100 ml) so as to separate the layer. Furthermore, the aqueous layer was extracted with ethyl acetate, and the organic layer was washed with 5% aqueous sodium hydrogen sulfite solution and saturated saline. The resulting mixture was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. To the residue were added ethyl acetate (50 ml) and hexane (100 ml) and the resulting mixture was stirred for fifteen minutes, and the precipitated solids were then collected by filtration and washed with hexane to afford 5-iodo-1-(3-(trifluoromethyl)phenyl)pyrimidin-2,4(1H,3H)-dione (7.34 g).

1. temperatureThe resulting mixture was cooled to 0° C.
2. customadded ethyl acetate (150 ml), saturated saline (50 ml) and 5% sodium hydrogen sulfite solution (100 ml) so as to separate the layer
3. extractionFurthermore, the aqueous layer was extracted with ethyl acetate
4. washthe organic layer was washed with 5% aqueous sodium hydrogen sulfite solution and saturated saline
5. dry with materialThe resulting mixture was dried over anhydrous magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. additionTo the residue were added ethyl acetate (50 ml) and hexane (100 ml)
8. stirringthe resulting mixture was stirred for fifteen minutes
9. filtrationthe precipitated solids were then collected by filtration
10. washwashed with hexane

ORD record

ord-8afe8595f15e41f890046e2cae0f83a5

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09040516B2