Bromine → 5-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione

温度

55 °C

Bromine (0.497 mL, 9.68 mmol) was added to a solution of 5-benzoyl-1,3,6-trimethyl pyrimidine-2,4(1H,3H)-dione (step 2) (2.5 g, 9.68 mmol) in chloroform (50 mL) with stirring under nitrogen. The mixture was then heated to 55° C. for 2 h. A further portion of bromine (0.25 mL, 0.5 equiv) was then added and heating continued at 55° C. for a further 30 min. The mixture was then cooled to RT, diluted with CHCl3 (50 mL) and poured into saturated sodium thiosulfate solution (150 mL). The layers were separated and the aqueous phase was extracted with CHCl3 (50 mL). The combined organics were washed with water (50 mL), brine (50 mL), dried (Na2SO4) and filtered under reduced pressure. The solvent was then evaporated under reduced pressure to afford a pale yellow solid. This solid was dissolved in hot EtOAc (50 mL) and slowly evaporated until crystallisation was observed. The resulting white solid was collected by reduced pressure filtration and washed with cold EtOAc (10 mL) and dried in air. The compound was further dried under vacuum at 50° C. for 2 h. The title product was isolated as white micro needles.

1. temperatureheating
2. temperatureThe mixture was then cooled to RT
3. customThe layers were separated
4. extractionthe aqueous phase was extracted with CHCl3 (50 mL)
5. washThe combined organics were washed with water (50 mL), brine (50 mL)
6. dry with materialdried (Na2SO4)
7. filtrationfiltered under reduced pressure
8. customThe solvent was then evaporated under reduced pressure
9. customto afford a pale yellow solid
10. customslowly evaporated until crystallisation
11. filtrationThe resulting white solid was collected by reduced pressure filtration
12. washwashed with cold EtOAc (10 mL)
13. customdried in air
14. customThe compound was further dried under vacuum at 50° C. for 2 h

ORDレコード

ord-ba996fcd628e43ac81fcdde45d758148

出典データセット

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09359381B2