Malonic Acid → HCID 90251647, compound

Temperature

80 °C

1-Methyl-3-(3-(trifluoromethyl)phenyl)urea (available from Crescent Chemical Co., Inc.) (4.03 g) and malonic acid (2.11 g) were suspended into acetic anhydride (12 ml) and the resulting mixture was stirred at 80° C. for one hour. After the reaction solutions were concentrated under reduced pressure, to the residue was added saturated aqueous sodium hydrogen carbonate solution and the resulting mixture was washed with ethyl acetate. The aqueous layer was acidified with concentrated hydrochloric acid and the resulting mixture was extracted with ethyl acetate (50 ml×2). The organic layer was washed with saturated saline (50 ml), dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol) to afford 1-methyl-3-(3-(trifluoromethyl)phenyl)pyrimidin-2,4,6-(1H, 3H, 5H)-trione (2.75 g).

1. concentrationAfter the reaction solutions were concentrated under reduced pressure, to the residue
2. additionwas added saturated aqueous sodium hydrogen carbonate solution
3. washthe resulting mixture was washed with ethyl acetate
4. extractionthe resulting mixture was extracted with ethyl acetate (50 ml×2)
5. washThe organic layer was washed with saturated saline (50 ml)
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol)

ORD record

ord-aecfbc25544a4933b0ac0eb191adf1b4

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09040516B2