Azepane → Methyl 2-(4-(azepan-1-yl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoate
Reaktionsgleichung
[NH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:16]1[C:21]([CH:22]([CH2:27][CH2:28][CH3:29])[C:23]([O:25][CH3:26])=[O:24])=[C:20]([CH3:30])[N:19]=[C:18]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:17]=1>O1CCCC1.C(=O)([O-])O.[Na+]>[N:1]1([C:16]2[C:21]([CH:22]([CH2:27][CH2:28][CH3:29])[C:23]([O:25][CH3:26])=[O:24])=[C:20]([CH3:30])[N:19]=[C:18]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[N:17]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
Azepane (0.113 mL; 1.00 mmol) and triethylamine (0.277 mL; 2.00 mmol) were added to a solution of methyl 2-(4-chloro-6-methyl-2-phenylpyrimidin-5-yl)pentanoate (0.159 g; 0.5 mmol) in tetrahydrofuran (1.5 mL). The reaction vessel was sealed and heated at 100° C. for 18 h. The mixture was diluted with a saturated solution of sodium hydrogen carbonate and was extracted with ethyl acetate. The combined organics were washed with brine, dried over magnesium sulphate, filtered and concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-40%) in heptane furnished 0.092 g (98%) of the title compound.
Aufarbeitung
- customThe reaction vessel was sealed
- extractionwas extracted with ethyl acetate
- washThe combined organics were washed with brine
- dry with materialdried over magnesium sulphate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customPurification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-40%) in heptane
Quellen und Nachweise
- ORD-Eintrag
- ord-16af6219f0044db68b78460d3daad63a
- Quelldatensatz
- uspto-grants-2014_12
- Patentnummer
- US08906906B2
Notizen zur Reaktion
Wird geladen…