반응 #1554

반응 방정식

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

sodium trifluoroacetate

N-methylpyrrolidinone

→

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

수율 42.2%

용매

ether

반응 조건

후처리

1. 1
   온도was heated at 175 C for 2 h
2. 2
   온도The mixture was cooled
3. 3
   세척washed with four 50 mL portions of water
4. 4
   건조dried over MgSO4
5. 5
   기타Removal of the solvent on the rotovap
6. 6
   기타afforded 0.92 g of crude product as a brown oil
7. 7
   기타This 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

실험 절차

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).

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