Water → 5-benzoyl-1,3,6-trimethyl-2,4(1H,3H)-Pyrimidinedione

Temperature

110 °C

1,3,6-Trimethylpyrimidine-2,4(1H,3H)-dione (step 1) (5 g, 32.4 mmol) and chlorobenzene (50 mL) were charged to a 3 necked flask, and the vessel evacuated with nitrogen. Benzoyl chloride (commercial) (11.2 mL, 97 mmol) was added followed by zinc (II) chloride (5 g, 36.7 mmol) in one portion and the reaction was heated to 110° C. for 16 h. The reaction was cooled to RT then poured into water (100 mL) and EtOAc (100 mL). The layers were separated and the aqueous extracted with EtOAc (2×150 mL). The combined organics were washed with water (100 mL) and dried (Na2SO4), filtered under reduced pressure and evaporated to leave an orange solid. The solid was washed with hexane followed by hot diethyl ether, affording the product as an off white solid. The mother liquors were further purified by chromatography on silica, eluting with 10%-100% EtOAc/hexane. The title product was obtained as a pale orange solid.

1. customthe vessel evacuated with nitrogen
2. temperatureThe reaction was cooled to RT
3. customThe layers were separated
4. extractionthe aqueous extracted with EtOAc (2×150 mL)
5. washThe combined organics were washed with water (100 mL)
6. dry with materialdried (Na2SO4)
7. filtrationfiltered under reduced pressure
8. customevaporated
9. customto leave an orange solid
10. washThe solid was washed with hexane
11. customaffording the product as an off white solid
12. customThe mother liquors were further purified by chromatography on silica
13. washeluting with 10%-100% EtOAc/hexane

ORD record

ord-9f1bcb5dcddc4d56af2ac370762ad325

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09303035B2