Hydrochloric Acid → 1-(6-Chloropyrimidin-4-yl)ethan-1-one

4-Chloro-6-[1-(ethyloxy)ethenyl]pyrimidine (Intermediate 17, 564 mg, 3.05 mmol) was dissolved in acetone (15 mL), treated with 2M aqueous hydrochloric acid solution (2.291 mL, 4.58 mmol) and the resulting mixture was stirred at room temperature for 2.5 hours. A further amount of 2M aqueous hydrochloric acid solution (2.291 mL, 4.58 mmol) was added and the resulting mixture was stirred at room temperature for 18 hours. The solvent was removed under reduced pressure, the residue taken up in DCM and washed with saturated sodium bicarbonate solution. The DCM layer was separated and the aqueous layer was extracted with DCM (×2). The DCM layers were separated, combined, dried under magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (Biotage SP4) eluting with a gradient of 0-30% ethyl acetate and iso-hexane. Product containing fractions were combined and evaporated under reduced pressure to give the title compound as a white solid (32 mg);

1. stirringthe resulting mixture was stirred at room temperature for 18 hours
2. customThe solvent was removed under reduced pressure
3. washwashed with saturated sodium bicarbonate solution
4. customThe DCM layer was separated
5. extractionthe aqueous layer was extracted with DCM (×2)
6. customThe DCM layers were separated
7. customdried under magnesium sulfate
8. customevaporated under reduced pressure
9. customThe residue was purified by column chromatography (Biotage SP4)
10. washeluting with a gradient of 0-30% ethyl acetate and iso-hexane
11. additionProduct containing fractions
12. customevaporated under reduced pressure

ORDレコード

ord-24f95cd9c0de458cbf0fc2b67efe5e5b

出典データセット

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08796283B2