Réaction #1554

Équation de réaction

3,6-diethyl-5-iodo-2-phenyl-4(3H)-pyrimidinone

sodium trifluoroacetate

N-methylpyrrolidinone

→

3,6-diethyl-2-phenyl-5-trifluoromethyl-4(3H)-pyrimidinone

Rendement 42.2%

Solvants

ether

Conditions de réaction

Traitement

1. 1
   Températurewas heated at 175 C for 2 h
2. 2
   TempératureThe mixture was cooled
3. 3
   Lavagewashed with four 50 mL portions of water
4. 4
   Séchagedried over MgSO4
5. 5
   AutreRemoval of the solvent on the rotovap
6. 6
   Autreafforded 0.92 g of crude product as a brown oil
7. 7
   AutreThis material was purified by flash chromatography on a 25 g column of silica gel eluting with 100 mL portions of 0, 10, 20, 30, 40, 50 and 75% ether in hexanes

Mode opératoire

A mixture of 1.00 g (2.8 mmol) of 3,6-diethyl-5-iodo-2-phenyl-4(3H)-pyrimidinone, 1.08 g (5.7 mmol) of copper (I) iodide, 1.54 g (11.3 mmol) of sodium trifluoroacetate and 8 mL of anhydrous N-methylpyrrolidinone was heated at 175 C for 2 h. The mixture was cooled, diluted with 175 mL of ether, washed with four 50 mL portions of water and dried over MgSO4. Removal of the solvent on the rotovap afforded 0.92 g of crude product as a brown oil. This material was purified by flash chromatography on a 25 g column of silica gel eluting with 100 mL portions of 0, 10, 20, 30, 40, 50 and 75% ether in hexanes to afford 0.35 g of 3,6-diethyl-2-phenyl-5-trifluoromethyl-4(3H)-pyrimidinone (compound 185) as a white solid. 1H-NMR (CDCl3) 1.25(3H,t), 1.30(3H,t), 2.8(2H,q), 4.0(2H,q), 7.5(5H).

Source