Hydrochloric Acid → 6-[bis(2,4-dimethoxybenzyl)amino]-2-thioxo-3-[4-(2,2,2-trifluoroethoxy)phenyl]-2,3-dihydropyrimidin-4(1H)-one

To a solution of 1-isothiocyanato-4-(2,2,2-trifluoroethoxy)benzene (3.96 g) in N,N-dimethylformamide (120 mL) was added sodium hydride (60% in oil, 0.68 g) under ice-cooling. The reaction mixture was stirred for 5 min under ice-cooling, ethyl (2E)-3-amino-3-[bis(2,4-dimethoxybenzyl)amino]prop-2-enoate (7.3 g) was added thereto, and the mixture was stirred for 30 min under ice-cooling. To the reaction mixture was added 1M hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was dissolved in ethanol (120 mL), sodium ethoxide (20% ethanol solution, 14.5 mL) was added thereto, and the mixture was stirred for 1 hr. To the reaction mixture was added 1M hydrochloric acid, and the precipitated solid was collected by filtration to give the title compound (2.8 g).

1. temperaturecooling
2. temperaturecooling
3. stirringthe mixture was stirred for 30 min under ice-
4. temperaturecooling
5. extractionthe mixture was extracted with ethyl acetate
6. washThe extract was washed with saturated brine
7. dry with materialdried over anhydrous sodium sulfate
8. customThe solvent was evaporated under reduced pressure
9. dissolutionThe residue was dissolved in ethanol (120 mL)
10. additionsodium ethoxide (20% ethanol solution, 14.5 mL) was added
11. stirringthe mixture was stirred for 1 hr
12. additionTo the reaction mixture was added 1M hydrochloric acid
13. filtrationthe precipitated solid was collected by filtration

ORD-Eintrag

ord-49ea6ed81c804d2fbc89dd68dcead293

Quelldatensatz

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09023858B2