Water → HCID 22248034, compound

HRID 890052Notes

Reaction equation

HRID 890052 reaction equation
C[O:2][CH:3](OC)[C:4]1[C:9]([O:10][CH3:11])=[N:8][C:7](Cl)=[CH:6][N:5]=1.[CH3:15][Zn]C.O>O1CCCC1.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:11][O:10][C:9]1[C:4]([CH:3]=[O:2])=[N:5][CH:6]=[C:7]([CH3:15])[N:8]=1

Participants

6

Reactant 3

HCID 962WaterHCID 22248394HCID 22248394, compoundHCID 178477796HCID 178477796, compound

Product 1

HCID 22248034HCID 22248034, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 178418745HCID 178418745, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

After dissolving 3.34 g of 5-chloro-3-methoxypyrazine-2-carboxaldehyde dimethylacetal in 50 ml of tetrahydrofuran, 400 mg of [1,3-bis(diphenylphosphino)propane]dichloronickel(II) was added, 9.17 ml of dimethyl zinc (2.0 M, toluene solution) was added dropwise under a nitrogen atmosphere, and the mixture was stirred at room temperature for 2 hours and then at 50° C. for 1.5 hours. The reaction solution was cooled on ice, water was added and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine in that order and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was dissolved in 16 ml of acetone, 4 ml of 5N hydrochloric acid was added and the mixture was all owed to stand at room temperature for 15 minutes. A sodium bicarbonate solution was added to the reaction solution and extraction was performed with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (1.43 g, 61% yield).

Workup

  1. additionwas added
  2. waitat 50° C. for 1.5 hours
  3. additionwas added
  4. extractionextraction
  5. washThe organic layer was washed with water and saturated brine in that order
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. dissolutionThe residue was dissolved in 16 ml of acetone
  9. addition4 ml of 5N hydrochloric acid was added
  10. waitto stand at room temperature for 15 minutes
  11. additionA sodium bicarbonate solution was added to the reaction solution and extraction
  12. washThe organic layer was washed with saturated brine
  13. dry with materialdried over anhydrous magnesium sulfate
  14. distillationthe solvent was distilled off under reduced pressure
  15. customThe residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f1a91fe9de024c8885139f6bfc5ca90e
Source dataset
uspto-grants-2006_02
Patent number
US06995144B2

Reaction notes

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