Pyrazine → HCID 14220979, compound

HRID 986004Notes

Reaction equation

HRID 986004 reaction equation
C([Li])(C)(C)C.[CH3:6][O:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=2)[N:9]=1.[N:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1>CCCCC.C1COCC1>[CH3:6][O:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:20]3[CH:21]=[N:22][CH:23]=[CH:24][N:19]=3)[CH:14]=2)[N:9]=1

Participants

6

Reactant 3

HCID 9261PyrazineHCID 106575386-Bromo-2-methoxyquinolineHCID 178418306HCID 178418306, compound

Product 1

HCID 14220979HCID 14220979, compound

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

t-Butyl lithium (4.6 cm3 of a 2.6M solution in pentane) was added dropwise to a stirred solution of 2-methoxy-6-bromoquinoline (1.43 g) in THF (10 cm3) at -70° under nitrogen. After 20 minutes a solution of pyrazine (0.48 g) in THF (5 cm3) was added and after stirring for a further 20 minutes a stream of dry air was bubbled through the solution for 0.5 hour at -70° and then for a further 1 hour as the mixture warmed to room temperature. Chloroform (50 cm3) was added and the solution was washed with water (10 cm3), dried (MgSO4) and concentrated in vacuo to afford a residue which was chromatographed on silica (Merck "MK 60.9385") eluting with ethyl acetate:hexane, 1:1, to give a solid. Recrystallisation from ethyl acetate gave 2-methoxy-6-(2-pyrazinyl)quinoline. 1/4H2O, m.p. 130°-132°, (0.22 g).

Workup

  1. customwas bubbled through the solution for 0.5 hour at -70°
  2. additionChloroform (50 cm3) was added
  3. washthe solution was washed with water (10 cm3)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto afford a residue which
  7. customwas chromatographed on silica (Merck "MK 60.9385")
  8. washeluting with ethyl acetate
  9. customhexane, 1:1, to give a solid
  10. customRecrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-e3b41a80a14446c4bf8d4fdcc7c7bd52
Source dataset
uspto-grants-1987_12
Patent number
US04710507

Reaction notes

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