1-Butanol → (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine
Reaktionsgleichung
Cl[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][CH:10]=[C:4]2[N:3]=1.[F:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[C@H:19]1[CH2:23][CH2:22][CH2:21][NH:20]1.C(O)CCC.CCN(C(C)C)C(C)C>CCOC(C)=O>[F:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[C@H:19]1[CH2:23][CH2:22][CH2:21][N:20]1[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][CH:10]=[C:4]2[N:3]=1Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 160 °C
Versuchsvorschrift
In a pressure reaction tube was added 5-chloropyrazolo[1,5-a]pyrimidine (4.2 g, 27 mmol), (R)-2-(2,5-difluorophenyl)pyrrolidine (Preparation A; 5.3 g, 29 mmol), anhydrous n-butanol (5 ml, 55 mmol), and DIEA (9.5 ml, 55 mmol). The yellowish suspension was sealed and heated in an oil bath (160° C.) overnight. The reaction was cooled to ambient temperature, diluted with EtOAc (250 mL), and filtered, rinsing the solid with EtOAc. The filtrate (330 mL) was washed with water (2×150 mL), brine (100 mL), concentrated, and purified by silica chromatography, eluting with 2:1 EtOAc/hexanes to give the product as a bright yellowish solid (5.6 g, 68% yield).
Aufarbeitung
- customIn a pressure reaction tube
- customPreparation A
- customThe yellowish suspension was sealed
- temperatureThe reaction was cooled to ambient temperature
- filtrationfiltered
- washrinsing the solid with EtOAc
- washThe filtrate (330 mL) was washed with water (2×150 mL), brine (100 mL)
- concentrationconcentrated
- custompurified by silica chromatography
- washeluting with 2:1 EtOAc/hexanes
Quellen und Nachweise
- ORD-Eintrag
- ord-f585e131793a4c13ac03bf68c03b509b
- Quelldatensatz
- uspto-grants-2016_09
- Patentnummer
- US09447104B2
Notizen zur Reaktion
Wird geladen…