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
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).
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