N,N'-Dimethylethylenediamine → HCID 57540632, compound

HRID 906232Notes

Reaction equation

HRID 906232 reaction equation
[F:1][C:2]([F:19])([F:18])[O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[C:12](=[O:17])[NH:13][CH:14]=[CH:15][N:16]=2)=[CH:6][CH:5]=1.Br[C:21]1[CH:32]=[CH:31][C:24]([O:25][CH2:26][C:27]([CH3:30])([OH:29])[CH3:28])=[C:23]([CH3:33])[CH:22]=1.CNCCNC.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cu]I>[OH:29][C:27]([CH3:30])([CH3:28])[CH2:26][O:25][C:24]1[CH:31]=[CH:32][C:21]([N:13]2[CH:14]=[CH:15][N:16]=[C:11]([S:10][C:7]3[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:18])[F:19])=[CH:9][CH:8]=3)[C:12]2=[O:17])=[CH:22][C:23]=1[CH3:33]

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 57540531HCID 57540531, compoundHCID 57540533HCID 57540533, compound

Product 1

HCID 57540632HCID 57540632, compoundYield 11.52%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 3-(4-(trifluoromethoxy)phenylthio)pyrazin-2(1H)-one (100 mg, 0.347 mmol), 1-(4-bromo-2-methylphenoxy)-2-methylpropan-2-ol (90 mg, 0.347 mmol), N1,N2-dimethylethane-1,2-diamine (92 mg, 1.041 mmol), copper(I) iodide (19.82 mg, 0.104 mmol) and K3PO4 (221 mg, 1.041 mmol) in dioxane (1.0 mL) was stirred at 115° C. in a sealed tube for 2 hours. After removal of the precipitate by filtration, the filtrate was concentrated. The crude product was purified by silica gel chromatography employing a solvent gradient (hexane to 100% EtOAc) to elute 1-(4-(2-hydroxy-2-methylpropoxy)-3-methylphenyl)-3-(4-(trifluoromethoxy)phenylthio)-pyrazin-2(1H)-one (18.65 mg, 0.040 mmol, 11.52% yield) as off-white solid. 1H NMR (500 MHz, methanol-d3) δ ppm 7.62-7.68 (2H, m), 7.37 (2H, d, J=7.97 Hz), 7.21-7.28 (3H, m), 7.16 (1H, d, J=4.40 Hz), 7.02 (1H, d, J=8.25 Hz), 3.84 (2H, s), 2.31 (3H, s), 1.36 (6H, s).

Workup

  1. customAfter removal of the precipitate
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated
  4. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-3e9689ec541a490cb5f0b6301abf31c4
Source dataset
uspto-grants-2011_09
Patent number
US08012984B2

Reaction notes

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