Reaction #1554

Reaction equation

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

sodium trifluoroacetate

N-methylpyrrolidinone

→

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

Yield 42.2%

Solvents

ether

Conditions

Workup

1. 1
   Temperaturewas heated at 175 C for 2 h
2. 2
   TemperatureThe mixture was cooled
3. 3
   Washwashed with four 50 mL portions of water
4. 4
   Dryingdried over MgSO4
5. 5
   OtherRemoval of the solvent on the rotovap
6. 6
   Otherafforded 0.92 g of crude product as a brown oil
7. 7
   OtherThis 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

Procedure

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