Reaktionsgleichung
O[C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:13])[N:5]=[C:4]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[N:3]=1.CN(C)C1C=CC=CC=1.O=P(Cl)(Cl)[Cl:35]>>[Cl:35][C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:13])[N:5]=[C:4]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[N:3]=1Komponenten
4
Versuchsvorschrift
A solution of methyl [4-hydroxy-6-methyl-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate (1.59 g, 5.0 mmol) and N,N-dimethylaniline (0.56 mL, 4.4 mmol) in POCl3 (2.33 mL, 25 mmol) was refluxed for 14 hours. After cooling to room temperature, the reaction mixture was poured into ice-cold saturated K2CO3. The resulting aqueous layer was extracted with EtOAc and the combined organic extracts was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude product thus obtained was chromatographed over silica gel eluting with 20% EtOAc in n-hexane to afford methyl [4-chloro-6-methyl-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate (0.54 g, 32% yield) as a white powder.
Aufarbeitung
- additionthe reaction mixture was poured into ice-cold saturated K2CO3
- extractionThe resulting aqueous layer was extracted with EtOAc
- washthe combined organic extracts was washed with brine
- dry with materialdried over anhydrous MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude product thus obtained
- customwas chromatographed over silica gel eluting with 20% EtOAc in n-hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-2a257eac0af043d3a69762b1048df3dd
- Quelldatensatz
- uspto-grants-2010_10
- Patentnummer
- US07812160B2
Verknüpfte Notizen
Wird geladen…