Reaktion #952813

Reaktionsgleichung

3-[4-chloro-2-fluoro-5-(hydroxy)phenyl]-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

potassium carbonate

propargyl bromide

acetonitrile

→

title compound

3-[4-chloro-2-fluoro-5-[(2-propynyl)-oxy]phenyl]-1-(2-propynyl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe stirred mixture was then refluxed gently under nitrogen for 2 h
2. 2
   FiltrationThe solution was filtered
3. 3
   Waschenwashed with ethyl acetate
4. 4
   Einengenconcentrated in vacuo
5. 5
   Sonstigechromatographed over silica gel
6. 6
   Wascheneluting with a 1:4 v
7. 7
   workup.ADDITIONv mixture of ethyl acetate and hexane

Vorschrift

To a stirred solution of 500 mg (1.50 mmol) of 3-[4-chloro-2-fluoro-5-(hydroxy)phenyl]-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione in 20 mL of acetonitrile was added 425 mg (3.1 mmol) of potassium carbonate and 0.34 mL (3.10 mmol) of 80% solution of propargyl bromide in toluene. The stirred mixture was then refluxed gently under nitrogen for 2 h. The solution was filtered, washed with ethyl acetate, and concentrated in vacuo. The resulting yellow oil was flash chromatographed over silica gel, eluting with a 1:4 v:v mixture of ethyl acetate and hexane to give 90 mg of the title compound as a pale yellow oil: 1 -NMR (CDCl3, 200 MHz): ppm 7.35 (d, 1H), 7.0 (d, 1H), 6.4 (s, 1H), 4.75 (m, 4H), 2.6 (m, 1H), 2.4 (m, 1H). It also gives 150 mg of 3-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]phenyl]-1-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione as a yellow oil: 1 -NMR (DMSO-d6): ppm 7.7 (d, 1H), 7.4 (d, 1H), 6.4 (s, 1H), 4.8 (d, 2H), 2.5 (m, 1H).

Quelle