2-Methylfuran → 6-(5-Methylfuran-2-yl)-5-phenylpyrazin-2-ylamine

HRID 1710697Notes

Reaction equation

HRID 1710697 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[N:4][C:3]=1[C:9]1[CH:14]=[CH:13]N=[CH:11][CH:10]=1.[CH3:15][C:16]1[O:17][CH:18]=[CH:19][CH:20]=1.[C:21]([O-])(=O)C.[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C)C(=O)C>[CH3:15][C:16]1[O:17][C:18]([C:2]2[N:7]=[C:6]([NH2:8])[CH:5]=[N:4][C:3]=2[C:9]2[CH:10]=[CH:11][CH:21]=[CH:13][CH:14]=2)=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 107972-MethylfuranHCID 517044Potassium AcetateHCID 594576006-Chloro-5-pyridin-4-ylpyrazin-2-amine

Product 1

HCID 684967096-(5-Methylfuran-2-yl)-5-phenylpyrazin-2-ylamineYield 12.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 31374DimethylacetamideSolvent

Procedure

An oven dried resealable Schlenk tube was charged with 6-chloro-5-pyridin-4-ylpyrazin-2-amine (Preparation 7, 300 mg, 1.45 mmol), 2-methylfuran (1.31 mL, 14.5 mmol), potassium acetate (213 mg, 2.17 mmol) and N,N-dimethylacetamide (6 mL). The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon, and tetrakis(triphenylphosphine)palladium (117 mg, 0.10 mmol) was added. After three new cycles of evacuation-backfilling with argon, the Schlenk tube was capped and placed in a 150° C. oil bath. After 40 h, the mixture was cooled, partitioned between water and ethyl acetate, the aqueous phase extracted with ethyl acetate (×3), the organic layers washed with brine, dried (MgSO4) and evaporated. Flash chromatography (dichloromethane/methanol 98:2 to dichloromethane/methanol 90:10) furnished the title compound as a brown solid (45 mg, 12%).

Workup

  1. customAn oven dried resealable Schlenk tube
  2. additionwas added
  3. customAfter three new cycles of evacuation-backfilling with argon, the Schlenk tube was capped
  4. customplaced in a 150° C.
  5. temperaturethe mixture was cooled
  6. custompartitioned between water and ethyl acetate
  7. extractionthe aqueous phase extracted with ethyl acetate (×3)
  8. washthe organic layers washed with brine
  9. dry with materialdried (MgSO4)
  10. customevaporated

Sources & evidence

ORD record
ord-adebdf80c2fe444bb7ca2e511d362767
Source dataset
uspto-grants-2010_09
Patent number
US07790728B2

Reaction notes

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