Diethyl Ether → 3-Methyl-2,5-diphenylpyrazine

HRID 1464871Notes

Reaction equation

HRID 1464871 reaction equation
C(OCCCC)CCC.[C:10]1([Li])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(OCC)C.[CH3:22][C:23]1[C:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[N:27][CH:26]=[CH:25][N:24]=1>O>[CH3:22][C:23]1[C:28]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[N:27][CH:26]=[C:25]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:24]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8909Butyl etherHCID 125688282-Methyl-3-phenylpyrazineHCID 178506676HCID 178506676, compound

Product 1

HCID 133209913-Methyl-2,5-diphenylpyrazineYield 12%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a nitrogen atmosphere, 10 mL of a dibutyl ether solution containing phenyl lithium (produced by Wako Pure Chemical Industries, Ltd., 2.1 mol/L) and 120 mL of diethylether were mixed. While the mixed solution was being cooled with ice, 2.87 g of 2-methyl-3-phenylpyrazine was added thereto and stirred at a room temperature for 24 hours. Water was added into this mixture, and an organic layer was extracted with ethyl acetate. The organic layer obtained was dried with magnesium sulfate. The solution after drying was added with activated manganese dioxide excessively and filtration was conducted. A solvent of the obtained filtrate was distilled off, so that a residue was obtained. This residue was purified by silica gel column chromatography which uses dichloromethane as a developing solvent; thereby obtaining an objective pyrazine derivative Hmppr-P (orange oily substance, yield of 12%). A synthetic scheme of Step 1 is shown in the following (a-5).

Workup

  1. additionwere mixed
  2. additionwas added
  3. extractionan organic layer was extracted with ethyl acetate
  4. customThe organic layer obtained
  5. dry with materialwas dried with magnesium sulfate
  6. customThe solution after drying
  7. additionwas added with activated manganese dioxide excessively and filtration
  8. distillationA solvent of the obtained filtrate was distilled off, so that a residue
  9. customwas obtained
  10. customThis residue was purified by silica gel column chromatography which

Sources & evidence

ORD record
ord-6b1c5f7ad93c47108f53c74f23a128e6
Source dataset
uspto-grants-2015_04
Patent number
US08999520B2

Reaction notes

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