N-methyl-2-pyrrolidone → 3,6-diethyl-2-phenyl-5-trifluoromethyl-4(3H)-pyrimidinone

HRID 1458

반응식

HRID 1458 반응식
[CH2:1]([N:3]1[C:8](=[O:9])[C:7](I)=[C:6]([CH2:11][CH3:12])[N:5]=[C:4]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:2].[F:19][C:20]([F:25])([F:24])C([O-])=O.[Na+].CN1CCCC1=O>CCOCC.[Cu]I>[CH2:1]([N:3]1[C:8](=[O:9])[C:7]([C:20]([F:25])([F:24])[F:19])=[C:6]([CH2:11][CH3:12])[N:5]=[C:4]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:2]

참가 물질

6

반응물 3

HCID 13387N-methyl-2-pyrrolidoneHCID 517019Sodium TrifluoroacetateHCID 196906603,6-diethyl-5-iodo-2-phenyl-4(3H)-pyrimidinone

생성물 1

HCID 196907203,6-diethyl-2-phenyl-5-trifluoromethyl-4(3H)-pyrimidinone수율 42.2%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 3283Diethyl Ether용매

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).

후처리

  1. temperaturewas heated at 175 C for 2 h
  2. temperatureThe mixture was cooled
  3. washwashed with four 50 mL portions of water
  4. dry with materialdried over MgSO4
  5. customRemoval of the solvent on the rotovap
  6. customafforded 0.92 g of crude product as a brown oil
  7. customThis 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

출처 및 근거

ORD 기록
ord-5d84c8f338a741eebe88ed5f50eec903
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726124

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