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

HRID 1458

Reaktionsgleichung

Reaktionsgleichung von HRID 1458
[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]

Komponenten

6

Edukt 3

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

Produkt 1

HCID 196907203,6-diethyl-2-phenyl-5-trifluoromethyl-4(3H)-pyrimidinoneAusbeute 42,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-5d84c8f338a741eebe88ed5f50eec903
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726124

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