N,N'-Dimethylethylenediamine → HCID 25169199, compound

HRID 562602Notes

Reaction equation

HRID 562602 reaction equation
[CH2:1]([S:9][C:10]1[C:11](=[O:16])[NH:12][CH:13]=[CH:14][N:15]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[C:18]1[CH:29]=[CH:28][C:21]([O:22][CH2:23][C:24]([CH3:27])([OH:26])[CH3:25])=[C:20]([CH3:30])[CH:19]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CNCCNC>O1CCOCC1.[Cu](I)I>[OH:26][C:24]([CH3:27])([CH3:25])[CH2:23][O:22][C:21]1[CH:28]=[CH:29][C:18]([N:12]2[CH:13]=[CH:14][N:15]=[C:10]([S:9][CH2:1][CH2:2][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:11]2=[O:16])=[CH:19][C:20]=1[CH3:30]

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 57540533HCID 57540533, compoundHCID 57540566HCID 57540566, compound

Product 1

HCID 25169199HCID 25169199, compoundYield 57.5%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 3-(phenethylthio)pyrazin-2(1H)-one (25 mg, 0.108 mmol), which was prepared by the procedure described in Method 7 except for substitution of 2-phenethylthiol for 2-(4-chlorophenethanol), 1-(4-bromo-2-methylphenoxy)-2-methylpropan-2-ol (33.5 mg, 0.129 mmol), copper iodide (20.50 mg, 0.108 mmol), K3PO4 (70 mg, 0.323 mmol) and N,N′-dimethylethylenediamine (28.5 mg, 0.323 mmol) in dioxane (1.0 ml) was stirred at 115° C. for 2 hours. The reaction mixture, after cooling to RT, was filtered and the filtrate was concentrated. The crude product was purified by silica gel chromatography employing a solvent gradient (hexane to 100% ethyl acetate) to elute to yield 1-(4-(2-hydroxy-2-methylpropoxy)-3-methylphenyl)-3-(phenethylthio)-pyrazin-2(1H)-one (26.74 mg, 0.062 mmol, 57.5% yield) as off-white solid. MS (M+1=411). 1H NMR (500 MHz, methanol-d3) δ ppm 7.38 (1H, d, J=4.40 Hz), 7.25-7.32 (4H, m), 7.16-7.24 (4H, m), 7.00 (1H, d, J=8.25 Hz), 3.83 (1H, s), 3.24-3.39 (2H, m), 2.90-3.05 (2H, 2.29 (3H, s), 1.35 (6H, s).

Workup

  1. customwas prepared by the procedure
  2. temperatureThe reaction mixture, after cooling to RT
  3. filtrationwas filtered
  4. concentrationthe filtrate was concentrated
  5. customThe crude product was purified by silica gel chromatography
  6. washto elute

Sources & evidence

ORD record
ord-5f52ef94efd84369a7fbab54a28c7754
Source dataset
uspto-grants-2011_11
Patent number
US08067420B2

Reaction notes

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