Reacción #1554

Ecuación de reacción

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

sodium trifluoroacetate

N-methylpyrrolidinone

→

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

Rendimiento 42.2%

Disolventes

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated at 175 C for 2 h
2. 2
   TemperaturaThe mixture was cooled
3. 3
   Lavadowashed with four 50 mL portions of water
4. 4
   Secadodried over MgSO4
5. 5
   OtroRemoval of the solvent on the rotovap
6. 6
   Otroafforded 0.92 g of crude product as a brown oil
7. 7
   OtroThis 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

Procedimiento

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).

Fuente