Hydrochloric Acid → 5-(2-Ethoxy-ethyl)-pyrimidine-2,4,6-trione

Sodium metal (8.6 g, 0.38 mol) was added to ethanol (375 mL), and the mixture was stirred at ambient temperature until homogeneous. Diethyl malonate (60 g, 0.38 mol) was added, followed by bromoethyl ethyl ether (57.4 g, 0.38 mol). After stirring at reflux for 3 hours, the mixture was cooled to ambient temperature and concentrated in vacuo. The resulting material was added to a mixture of sodium ethoxide and ethanol (prepared by the reaction of 17.2 g of sodium metal with 600 mL of methanol). Urea (24 g) was added, and the resulting mixture was refluxed for 2.5 hours. After cooling to ambient temperature, the mixture was stirred for 12 hours, acidified with 1M hydrochloric acid solution, extracted three times with ethyl acetate, and the combined organic layers were dried over sodium sulfate (Na2SO4), filtered and concentrated in vacuo, affording 5-(2-ethoxy-ethyl)-pyrimidine-2,4,6-trione as a colorless solid.

1. stirringAfter stirring
2. temperatureat reflux for 3 hours
3. temperaturethe mixture was cooled to ambient temperature
4. concentrationconcentrated in vacuo
5. additionThe resulting material was added to a mixture of sodium ethoxide and ethanol (
6. customprepared by the reaction of 17.2 g of sodium metal with 600 mL of methanol)
7. temperaturethe resulting mixture was refluxed for 2.5 hours
8. temperatureAfter cooling to ambient temperature
9. stirringthe mixture was stirred for 12 hours
10. extractionextracted three times with ethyl acetate
11. dry with materialthe combined organic layers were dried over sodium sulfate (Na2SO4)
12. filtrationfiltered
13. concentrationconcentrated in vacuo

ORD-Eintrag

ord-c231ce5deda648a49df05045f30d520a

Quelldatensatz

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06706723B2