Reaktion #1246856

Reaktionsgleichung

methyl [4-hydroxy-6-methyl-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate

N,N-dimethylaniline

POCl3

→

methyl [4-chloro-6-methyl-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate

Ausbeute 32.2%

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONthe reaction mixture was poured into ice-cold saturated K2CO3
2. 2
   ExtraktionThe resulting aqueous layer was extracted with EtOAc
3. 3
   Waschenthe combined organic extracts was washed with brine
4. 4
   Trocknendried over anhydrous MgSO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigeThe crude product thus obtained
8. 8
   Sonstigewas chromatographed over silica gel eluting with 20% EtOAc in n-hexane

Vorschrift

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.

Quelle