[Cl:1][C:2]1[CH:3]=[N:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][N:24]=1>C(C(C)=O)C>[Cl:1][C:2]1[CH:7]=[N:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][N:24]=2)=[N:4][CH:3]=1After heating at reflux a mixture of 1.5 grams (0.0067 mole) 2-(5-chloropyrimidin-2-yloxy)phenol, 1.2 grams potassium carbonate, 1.3 grams 2-chloro-5-nitropyridine and 40 ml of methyl ethyl ketone, the reaction mixture was poured into excess H2 0 and the aqueous mixture extracted with ethyl ether (200 ml). The ether layer was washed with saturated NaHCO3, H2O, brine, dried (MgSO4), filtered, and evaporated to yield 2.3 grams of a yellow-orange oil which was purified by silica gel column chromatography (CH2Cl2 as the eluent). NMR (CDCl3): δ6.90 (d, 1H, pyridine ring proton), 7.35 (s, 4H, ArH), 8.25-8.50 (m, 1H, pyridine ring proton), 8.45 (s, 2H, pyrimidine ring protons), 8.95 (d, 1H, pyridine ring proton).
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