[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([NH2:18])[C:7]=1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].[H-].[Na+].[CH3:21][O:22][C:23]1[CH:28]=[C:27]([O:29][CH3:30])[N:26]=[C:25](S(C)(=O)=O)[N:24]=1.Cl.[Cl-].[Na+]>O1CCCC1>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:9])=[C:6]([NH:18][C:25]2[N:26]=[C:27]([O:29][CH3:30])[CH:28]=[C:23]([O:22][CH3:21])[N:24]=2)[CH:5]=[CH:4][CH:3]=1
Under a nitrogen atmosphere a solution of 5.2 grams (0.020 mole) of phenylmethyl 6-chloroanthranilate in 150 mL of tetrahydrofuran was stirred, and 0.8 gram (0.02 mole) of 60% sodium hydride in mineral was added in one portion. Upon completion of addition, the reaction mixture was stirred for 5 minutes, and the reaction mixture temperature was slowly brought to 50° C. After this time 4.3 grams (0.020 mole) of 4,6-dimethoxy-2-methylsulfonylpyrimidine (prepared as in Example 1, Steps A-C) was added in one portion. Upon completion of - addition, the reaction mixture was warmed to reflux where it was stirred for about 18 hours. The reaction mixture was cooled to ambient temperature and was poured into a solution of 50 mL of 3N hydrochloric acid and 200 mL of an aqueous solution saturated with sodium chloride. The mixture was extracted with three 250 mL portions of diethyl ether. The combined extracts were washed with one 250 mL portion of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil. The oil was adsorbed onto silica gel and was subjected to column chromatography on silica gel. Elution was accomplished with 20% ethyl acetate in hexane. The appropriate fractions were combined and concentrated under reduced pressure to yield 4.0 grams of phenylmethyl 6-chloro-2-(4,6-dimethoxypyrimidin-2-ylamino)benzoate. The nmr spectrum was consistent with the proposed structure.
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