Reaktionsgleichung
Br[CH:2]([CH3:15])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1)=O.[NH2:16][C:17]1[N:22]=[CH:21][CH:20]=[CH:19][N:18]=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH3:15][C:2]1[N:16]=[C:17]2[N:22]=[CH:21][CH:20]=[CH:19][N:18]2[C:3]=1[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1Komponenten
Reaktionsbedingungen
- Temperatur
- 95 °C
Versuchsvorschrift
Add 2-bromo-1-(4-(trifluoromethyl)phenyl)propan-1-one (100 g, 0.356 mol), 2-aminopyrimidine (33.85 g, 0.356 mol), and sodium bicarbonate (59.8 g, 0.811 mol) to toluene (500 mL) at 25 to 30° C. Heat the mixture to 90 to 100° C. and stir for 24 hours. Thereafter cool the mixture to 40 to 45° C., and distill the title compound under reduced pressure. Cool the distillate to 25 to 30° C.; add water (1 L); and stir the mixture 4 hours. Filter the mixture collecting the solid, and then wash the solid with a 10% solution of MTBE (200 mL) in hexane. Dry the solid under vacuum at 45 to 50° C. for 12 hours to give the title compound (35.4 g, 35% yield). 1H NMR (300 MHz, CDCl3) δ 8.58 (q, 1H), 8.24-8.26 (d, J=6.6 Hz, 1H), 8.00-8.02 (d, J=8.1 Hz, 2H), 7.72-7.75 (d, J=8.4 Hz, 2H), 6.92-6.96 dd, J=3.9 Hz and 4.2 Hz, 1H), 2.69 (s, 3H).
Aufarbeitung
- temperatureThereafter cool the mixture to 40 to 45° C.
- distillationdistill the title compound under reduced pressure
- temperatureCool the distillate to 25 to 30° C.
- stirringand stir the mixture 4 hours
- filtrationFilter the mixture
- customcollecting the solid
- washwash the solid with a 10% solution of MTBE (200 mL) in hexane
- customDry the solid under vacuum at 45 to 50° C. for 12 hours
Quellen und Nachweise
- ORD-Eintrag
- ord-04cb4cf8fb1041d0b7d4eae0d9b417b2
- Quelldatensatz
- uspto-grants-2014_02
- Patentnummer
- US08648200B2
Verknüpfte Notizen
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