Zurück
HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 336961Erstellt: 25. Oktober 2026

Triethyl Phosphate → Allyl (rac)-4-{4-cyano-2-[(1-methylethyl)sulfonyl]phenyl}-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylate

https://huagongshe.com/reaction/336961

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktTriethyl PhosphateHCID 6535—
EduktPhosphorus oxide (P4O10)HCID 14812—
Edukt(3-Trifluoromethylphenyl)ureaHCID 25712—
EduktAllyl acetoacetateHCID 70701—
Edukt4-Formyl-3-[(1-methylethyl)sulfonyl]benzonitrileHCID 58133848—
Lösungsmitteltert-Butyl methyl etherHCID 15413—
ProduktAllyl (rac)-4-{4-cyano-2-[(1-methylethyl)sulfonyl]phenyl}-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylateHCID 58133777—

Reaktionsbedingungen

Temperatur90 °C

Reaktionsschritte

The reaction was carried out under argon. Triethyl phosphate (1.049 g, 5.76 mmol) and diphosphorus pentoxide (0.454 g) were stirred at 40° C. overnight. The mixture was then diluted with MTBE (25 ml), and 4-formyl-3-[(1-methylethyl)sulfonyl]benzonitrile (0.759 g, 3.2 mmol), 1-[3-(tri-fluoromethyl)phenyl]urea (0.653 g, 3.2 mmol) and allyl acetoacetate (0.682 g, 4.8 mmol; 1.5 eq.) were added. The mixture was stirred under reflux for 6 h. The reaction mixture was then concentrated by distillative removal of MTBE and subsequently heated at 90° C. for a further 2 h. For work-up, residual solvent was removed under reduced pressure and the residue was suspended in MTBE (20 ml) and then filtered off with suction. The solid was washed with MTBE (2×10 ml). This gave 1.25 g (48% of theory) of the title compound.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08889700B2
Quelldatensatzuspto-grants-2014_11
ORD IDord-4fe3ec2edc72435584a961b47e28687d
Quellennotizuspto-grants-2014_11