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Iodoethylene → 5-ethyl-3-(pent-2-yn-4-en-1-yl)-2-phenyl-6-trifluoromethyl-4(3 H)-pyrimidinone

HRID 1456
Notes
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Reaction equation

HRID 1456 reaction equation
[CH2:1]([C:3]1[C:4](=[O:22])[N:5]([CH2:19][C:20]#[CH:21])[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:7][C:8]=1[C:9]([F:12])([F:11])[F:10])[CH3:2].[CH:23](I)=[CH2:24]>C(N(CC)CC)C.[Cu]I.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([C:3]1[C:4](=[O:22])[N:5]([CH2:19][C:20]#[C:21][CH:23]=[CH2:24])[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:7][C:8]=1[C:9]([F:12])([F:11])[F:10])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 68976IodoethyleneHCID 113473105-ethyl-2-phenyl-3-propargyl-6-trifluoromethyl-4(3H)-pyrimidinone

Product 1

HCID 196907165-ethyl-3-(pent-2-yn-4-en-1-yl)-2-phenyl-6-trifluoromethyl-4(3 H)-pyrimidinoneYield 28.4%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst
HCID 6102075
Dichlorobis(triphenylphosphine)palladium
Catalyst
HCID 8471TriethylamineSolvent

Procedure

To a deoxygenated solution of 1.01 g (3.28 mmol) of 5-ethyl-2-phenyl-3-propargyl-6-trifluoromethyl-4(3H)-pyrimidinone and 0.61 g (3.96 mmol) of vinyl iodide in 25 mL of triethylamine was added a mixture of 60 mg of copper (I) iodide and 60 mg of bis(triphenylphosphine) palladium (II) chloride. The mixture was stirred at room temperature for 22 h and rotovapped to remove the bulk of the triethylamine. The residue was taken up in 150 mL of ethyl acetate, washed with 75 mL of 5% aqueous hydrochloric acid, 75 mL of saturated aqueous sodium bicarbonate and 75 mL of brine, and dried. Removal of the solvent left 1.51 g of a brown tar. Flash chromatography on a column of 30 g of silica gel eluting with 20, 40, 60 and 60% ether in hexanes afforded 0.31 g of crude 5-ethyl-3-(pent-2-yn-4-en-1-yl)-2-phenyl-6-trifluoromethyl-4(3H)-pyrimidinone. A second chromatography yielded 0.25 g (23%) of pure 5-ethyl-3-(pent-2-yn-4-en-1-yl)-2-phenyl-6-trifluoromethyl-4(3H)-pyrimidinone (compound 111) as a solid, mp 104°-106° C. 1H-NMR (CDCl3) d 1.25(3H,t), 2.8(2H,q), 4.75(2H,s), 5.5-5.9(3H,m), 7.55(3H,m), 7.7(2H,m).

Workup

  1. customto remove the bulk of the triethylamine
  2. washwashed with 75 mL of 5% aqueous hydrochloric acid, 75 mL of saturated aqueous sodium bicarbonate and 75 mL of brine
  3. customdried
  4. customRemoval of the solvent
  5. waitleft 1.51 g of a brown tar

Sources & evidence

ORD record
ord-cbd7be36ef084343a7a9b531a9094d81
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05726124

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes