Pyrimidine → 2-Methoxy-6-(pyrimidin-4-yl)quinoline

HRID 986002Notes

Reaction equation

HRID 986002 reaction equation
C([Li])CCC.[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][CH:22]=[N:21][CH:20]=1.[Cl-].[NH4+].[Mn]([O-])(=O)(=O)=O.[K+]>CCCCCC.CCOCC.CC(C)=O>[CH3:6][O:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:24]3[CH:23]=[CH:22][N:21]=[CH:20][N:19]=3)[CH:14]=2)[N:9]=1

Participants

9

Reactant 5

HCID 9260PyrimidineHCID 25517Ammonium ChlorideHCID 516875Potassium PermanganateHCID 106575386-Bromo-2-methoxyquinolineHCID 178418339Butyllithium

Product 1

HCID 142209752-Methoxy-6-(pyrimidin-4-yl)quinoline

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

n-Butyl lithium (2.7 cm3 of a 1.5M solution in hexane) was added dropwise to a stirred suspension of 2-methoxy-6-bromoquinoline (0.95 g) in ether (5 cm3) at -70° under nitrogen. When all the solid material had dissolved a solution of pyrimidine (0.32 g) in ether (1 cm3) was added dropwise and the resulting solution was allowed to warm to room temperature. Saturated ammonium chloride solution (5 cm3) was added, the aqueous phase was extracted with chloroform (3×10 cm3) and the dried (MgSO4) extracts were concentrated in vacuo to give an oil. This residue was taken into acetone and treated dropwise with a solution of potassium permanganate (0.63 g) in acetone until the purple colour persisted. The mixture ws filtered through "Solkafloc" (Trademark) and concentrated in vacuo to give an oil which was chromatographed on silica (Merck "MK. 60.9385" [Trademark]) eluting with ethyl acetate:hexane, 1:1, to give a solid. Recrystallisation from ethyl acetate gave 2-methoxy-6-(4-pyrimidinyl)quinoline, m.p. 164°-165°, (0.54 g).

Workup

  1. additionwas added dropwise
  2. extractionthe aqueous phase was extracted with chloroform (3×10 cm3)
  3. dry with materialthe dried (MgSO4) extracts
  4. concentrationwere concentrated in vacuo
  5. customto give an oil
  6. filtrationThe mixture ws filtered through "Solkafloc" (Trademark)
  7. concentrationconcentrated in vacuo
  8. customto give an oil which
  9. customwas chromatographed on silica (Merck "MK. 60.9385" [Trademark])
  10. washeluting with ethyl acetate
  11. customhexane, 1:1, to give a solid
  12. customRecrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-9b33ad6f19a24b5192873a465af6db7f
Source dataset
uspto-grants-1987_12
Patent number
US04710507

Reaction notes

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