N,N'-Dimethylethylenediamine → 3-(4-chlorophenethoxy)-1-(4-(2-hydroxy-2-methylpropoxy)phenyl)pyrazin-2(1H)-one

HRID 562592

Reaction equation

HRID 562592 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][CH2:7][O:8][C:9]2[C:10](=[O:15])[NH:11][CH:12]=[CH:13][N:14]=2)=[CH:4][CH:3]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].Br[C:27]1[CH:38]=[CH:37][C:30]([O:31][CH2:32][C:33]([CH3:36])([OH:35])[CH3:34])=[CH:29][CH:28]=1.CNCCNC>O1CCOCC1.[Cu]I>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][O:8][C:9]2[C:10](=[O:15])[N:11]([C:27]3[CH:38]=[CH:37][C:30]([O:31][CH2:32][C:33]([OH:35])([CH3:34])[CH3:36])=[CH:29][CH:28]=3)[CH:12]=[CH:13][N:14]=2)=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 211863421-(4-Bromophenoxy)-2-methylpropan-2-olHCID 580924053-(4-chlorophenethoxy)pyrazin-2(1H)-one

Product 1

HCID 575405813-(4-chlorophenethoxy)-1-(4-(2-hydroxy-2-methylpropoxy)phenyl)pyrazin-2(1H)-oneYield 73.1%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of 3-(4-chlorophenethoxy)pyrazin-2(1H)-one (25 mg, 0.100 mmol), K3PO4. (63.5 mg, 0.299 mmol), copper (1) iodide (18.99 mg, 0.100 mmol), 1-(4-bromophenoxy)-2-methylpropan-2-ol and N,N′-dimethylethylenediamine (0.032 mL, 0.299 mmol) in dioxane (1.0 mL) was stirred at 110° C. for 60 min. After removal of the precipitate by filtration, the filtrate was concentrated. The crude product was purified by silica gel chromatography employing a solvent gradient (CH2Cl2 to 10% MeOH/CH2Cl2) to elute 3-(4-chlorophenethoxy)-1-(4-(2-hydroxy-2-methylpropoxy)phenyl)pyrazin-2(1H)-one (31.82 mg, 0.073 mmol, 73.1% yield) as white solid. 1H NMR (500 MHz, chloroform-d) δ ppm 7.32 (2H, d), 7.23-7.29 (4 H, m), 7.02 (2H, d), 6.84 (2H, s), 4.51 (2H, t, J=7.29 Hz), 3.83 (2H, s), 3.13 (2H, t, J=7.15 Hz), 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-a2621266a54442649f1528c594093f3a
Source dataset
uspto-grants-2011_11
Patent number
US08067420B2

Linked notes

Loading…