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

HRID 1463249Notes

Reaction equation

HRID 1463249 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolvent

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(2 H,q), 4.0(2H,q), 7.5(5H).

Workup

  1. temperaturewas heated at 175 C
  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

Sources & evidence

ORD record
ord-2bf463d3afed416083d98b599bfc4851
Source dataset
uspto-grants-1994_04
Patent number
US05300477

Reaction notes

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