Reaktion #56833

Reaktionsgleichung

3-(5-chloro-2-methoxy-phenyl)-3-oxopropionic acid ethyl ester

acetamidine hydrochloride

potassium carbonate

→

6-(5-chloro-2-methoxy-phenyl)-2-methyl-3H-pyrimidin-4-one

Ausbeute 68.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to room temperature
2. 2
   workup.ADDITIONthe mixture was poured into ice cold water
3. 3
   FiltrationThe solid was collected by filtration
4. 4
   Waschenwashed with water and ether
5. 5
   Sonstigedried under vacuum

Vorschrift

A mixture of 3-(5-chloro-2-methoxy-phenyl)-3-oxopropionic acid ethyl ester (0.9 g, 3.2 mmol), acetamidine hydrochloride (448 mg, 4.7 mmol) and potassium carbonate (1.3 g, 9.6 mmol) in ethanol (15 ml) was stirred at 100° C. in thick wall tube for 60 hours. After cooling to room temperature, the mixture was poured into ice cold water. The solid was collected by filtration, washed with water and ether and dried under vacuum to provide 6-(5-chloro-2-methoxy-phenyl)-2-methyl-3H-pyrimidin-4-one (530 mg, 68% yield) as a white powder. 1H NMR (DMSO-d6) δ 2.32 (s, 3H, CH3), 3.85 (s, 3H, CH3), 6.77 (s, 1H, CH, Ar), 7.15 (d, 1H, J=8.8 Hz, Ar), 7.45 (dd, 1H, J=8.8 Hz, J=2.9 Hz, Ar), 7.90 (d, 1H, J=2.9 Hz, Ar), 12.42 (s, 1H, NH).

Quelle