Dimethyl Sulfoxide → 2-(2-Chloro-4-methoxy-phenyl)-1-(5-methyl-pyrazin-2-yl)-ethanone

HRID 1097855Notes

Reaction equation

HRID 1097855 reaction equation
C(OC(=O)[CH:5]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=1[Cl:23])[C:6]([C:8]1[CH:13]=[N:12][C:11]([CH3:14])=[CH:10][N:9]=1)=[O:7])C.[Cl-].[Na+].O.CS(C)=O>C(OCC)(=O)C>[Cl:23][C:16]1[CH:17]=[C:18]([O:21][CH3:22])[CH:19]=[CH:20][C:15]=1[CH2:5][C:6]([C:8]1[CH:13]=[N:12][C:11]([CH3:14])=[CH:10][N:9]=1)=[O:7]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 5234Sodium ChlorideHCID 666991002-(2-Chloro-4-methoxy-phenyl)-3-(5-methyl-pyrazin-2-yl)-3-oxo-propionic acid ethyl ester

Product 1

HCID 666991242-(2-Chloro-4-methoxy-phenyl)-1-(5-methyl-pyrazin-2-yl)-ethanoneYield 67%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(2-chloro-4-methoxy-phenyl)-3-(5-methyl-pyrazin-2-yl)-3-oxo-propionic acid ethyl ester (700 mg, 2 mmol), sodium chloride (130 mg), water (55 mg) and DMSO (10 mL) was heated for 5 h to 140° C. Upon cooling, the reaction mixture was taken up in ethyl acetate and washed (water, brine). The organic layer was dried (Na2SO4), and the solvent was evaporated. Purification of the residue by column chromatography (silica gel, heptane:ethyl acetate=100:0-80:20) gave the title compound (370 mg, 67%). 1H NMR (300 MHz, CDCl3) □ 9.13 (1H, s), 8.54 (1H, s), 7.18 (1H, d), 6.97 (1H, d), 6.70 (1H, dd), 4.57 (2H, s), 3.80 (3H, s), 2.68 (3H, s); MS (m/e)=277.0 [MH+].

Workup

  1. temperaturewas heated for 5 h to 140° C
  2. temperatureUpon cooling
  3. washwashed (water, brine)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. customthe solvent was evaporated
  6. customPurification of the residue by column chromatography (silica gel, heptane:ethyl acetate=100:0-80:20)

Sources & evidence

ORD record
ord-e35a4ce5cc6c4adb8cf8bd9fa9157bc0
Source dataset
uspto-grants-2012_03
Patent number
US08143280B2

Reaction notes

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