Sodium Carbonate → Pyrazine, 3,5-dimethyl-2-(7-phenyl-2-naphthalenyl)-

HRID 2173746Notes

Reaction equation

HRID 2173746 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[N:6][C:5]([CH3:9])=[CH:4][N:3]=1.[C:10]1([C:16]2[CH:25]=[C:24]3[C:19]([CH:20]=[CH:21][C:22](B(O)O)=[CH:23]3)=[CH:18][CH:17]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.C(#N)C>[CH3:8][C:7]1[C:2]([C:22]2[CH:21]=[CH:20][C:19]3[C:24](=[CH:25][C:16]([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)=[CH:17][CH:18]=3)[CH:23]=2)=[N:3][CH:4]=[C:5]([CH3:9])[N:6]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 116726802-Chloro-3,5-dimethylpyrazineHCID 58461088HCID 58461088, compound

Product 1

HCID 58461051Pyrazine, 3,5-dimethyl-2-(7-phenyl-2-naphthalenyl)-Yield 65%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

First, into a recovery flask equipped with a reflux pipe were placed 0.62 g of 2-chloro-3,5-dimethylpyrazine, 1.07 g of 7-phenylnaphthalene-2-boronic acid, 0.46 g of sodium carbonate, 0.020 g of bis(triphenylphosphine)palladium(II) dichloride (abbreviation: Pd(PPh3)2Cl2), 10 mL of water, and 10 mL of acetonitrile, and the air in the flask was replaced with argon. This reaction container was irradiated with microwaves (2.45 GHz, 100 W) for 15 minutes, so that heating was performed. Then, the reaction container was cooled to 50° C. or less. Water was added to the reaction solution, and the organic layer was extracted with dichloromethane. The obtained organic layer was washed with water and dried with magnesium sulfate. The solution which had been dried was filtered. The solvent of this solution was distilled, and the obtained residue was purified by silica gel column chromatography with a developing solvent of dichloromethane, whereby Hdm7p2npr, which is the pyrazine derivative to be produced, was found to be obtained (as a white powder in 65% yield). Note that the microwave irradiation was performed using a microwave synthesis system (Discover, manufactured by CEM Corporation). The synthesis scheme of Step 4 is illustrated in the following (d-5).

Workup

  1. customFirst, into a recovery flask equipped with a reflux pipe
  2. customThis reaction container was irradiated with microwaves (2.45 GHz, 100 W) for 15 minutes
  3. temperatureso that heating
  4. temperatureThen, the reaction container was cooled to 50° C. or less
  5. extractionthe organic layer was extracted with dichloromethane
  6. washThe obtained organic layer was washed with water
  7. dry with materialdried with magnesium sulfate
  8. customThe solution which had been dried
  9. filtrationwas filtered
  10. distillationThe solvent of this solution was distilled
  11. customthe obtained residue was purified by silica gel column chromatography with a developing solvent of dichloromethane, whereby Hdm7p2npr, which
  12. customto be produced
  13. customto be obtained (as a white powder in 65% yield)
  14. customNote that the microwave irradiation
  15. customa microwave synthesis system (Discover, manufactured by CEM Corporation)
  16. customThe synthesis scheme of Step 4

Sources & evidence

ORD record
ord-f6dbd2c7f726496ab8ee1c3ba8aef7ea
Source dataset
uspto-grants-2015_06
Patent number
US09056883B2

Reaction notes

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