Hydrochloric Acid → 4-Chloro-6-ethyl-5-fluoropyrimidine

Phosphorus oxychloride (0.787 mL, 8.44 mmol) was added slowly over 10 min to a mixture of 6-ethyl-5-fluoropyrimidin-4(1H)-one (1 g, 7.04 mmol) (Apollo Scientific) and triethylamine (0.981 mL, 7.04 mmol) in DCM (15 mL), keeping the reaction temperature below 40° C. The mixture was then heated to reflux for 5 hrs then cooled to room temperature. The reaction mixture was then slowly poured into aqueous HCl (4M, 20 mL), keeping the temp below 20° C. The organic layer was collected and the aqueous layer was further extracted with DCM (20 mL). The organic layers were combined then washed with water (20 mL), dried (MgSO4) filtered and the solvent was removed to give the title compound as a colourless oil (1 g).

1. customthe reaction temperature below 40° C
2. temperatureThe mixture was then heated
3. temperatureto reflux for 5 hrs
4. customthe temp below 20° C
5. customThe organic layer was collected
6. extractionthe aqueous layer was further extracted with DCM (20 mL)
7. washThe organic layers were combined then washed with water (20 mL)
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. customthe solvent was removed

ORD record

ord-ef5ee33fdb2f454ab5e19c4cc5104e71

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796283B2