N-Methylcyclohexylamine → Methyl 2-(2-(cyclohexyl(methyl)amino)-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate
Reaktionsgleichung
Cl[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH:9]([CH2:14][CH2:15][CH3:16])[C:10]([O:12][CH3:13])=[O:11])=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[N:3]=1.[CH3:24][NH:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>C1COCC1.C(=O)([O-])O.[Na+]>[CH:26]1([N:25]([CH3:24])[C:2]2[N:7]=[C:6]([CH3:8])[C:5]([CH:9]([CH2:14][CH2:15][CH3:16])[C:10]([O:12][CH3:13])=[O:11])=[C:4]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)[N:3]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1Komponenten
5
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
A mixture of methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate (100 mg; 0.30 mmol) and N-methylcyclohexanamine (0.158 mL; 1.202 mmol) in THF (1 mL) was placed in a sealed tube and heated at 100° C. for 18 h. The reaction mixture was diluted with a saturated sodium hydrogen carbonate solution and extracted twice with ethyl acetate. The organic layers were combined, washed with brine, dried over magnesium sulphate and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (2-20%) in heptane to give 61 mg (49%) of the title compound.
Aufarbeitung
- customwas placed in a sealed tube
- extractionextracted twice with ethyl acetate
- washwashed with brine
- dry with materialdried over magnesium sulphate
- concentrationconcentrated under reduced pressure
- customThe crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (2-20%) in heptane
Quellen und Nachweise
- ORD-Eintrag
- ord-8cc3e8cd481c49a7a733acc7782bd9a5
- Quelldatensatz
- uspto-grants-2014_12
- Patentnummer
- US08906906B2
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