تفاعل #1554

معادلة التفاعل

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

sodium trifluoroacetate

N-methylpyrrolidinone

→

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

المردود 42.2%

المذيبات

ether

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas heated at 175 C for 2 h
2. 2
   درجة الحرارةThe mixture was cooled
3. 3
   غسيلwashed with four 50 mL portions of water
4. 4
   تجفيفdried over MgSO4
5. 5
   أخرىRemoval of the solvent on the rotovap
6. 6
   أخرىafforded 0.92 g of crude product as a brown oil
7. 7
   أخرىThis 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

الإجراء التجريبي

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).

المصدر