C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(/C(OCC)=O)=N\C(OCC)=O.[Cl:32][C:33]1[C:34]([OH:40])=[CH:35][C:36](=[O:39])[NH:37][CH:38]=1.[Cl:41][C:42]1[CH:43]=[N:44][C:45]([N:48]2[CH2:53][CH2:52][CH:51](O)[CH2:50][CH2:49]2)=[N:46][CH:47]=1>CCCCCC.CCOCC.CN(C=O)C>[Cl:32][C:33]1[C:34]([O:40][CH:51]2[CH2:50][CH2:49][N:48]([C:45]3[N:46]=[CH:47][C:42]([Cl:41])=[CH:43][N:44]=3)[CH2:53][CH2:52]2)=[CH:35][C:36](=[O:39])[NH:37][CH:38]=1To a 200 mL recovery flask was added triphenylphosphine (7.34 g, 28.0 mmol) and DMF (40 mL) to produce a nearly complete solution with 2-3 minutes of stirring. To this mixture was added (E)-diethyl diazene-1,2-dicarboxylate (3.80 mL, 24.00 mmol). After stirring at room temperature for 5 minutes, 5-chloro-4-hydroxypyridin-2(1H)-one (Gimeracil) (5.82 g, 40.0 mmol) was added. After stirring at room temperature for 5 minutes, 1-(5-chloropyrimidin-2-yl)piperidin-4-ol (4.27 g, 20 mmol) was added. The reaction mixture was placed under a nitrogen line with a vent and placed in a 100° C. oil bath for 115 minutes. After cooling to room temperature, the clear brown reaction mixture was added to 1000 mL of ether with stirring which resulted in the formation of a tan-pink oily precipitate. To this mixture was added 500 mL of hexane. The mixture was stirred for 5 minutes and then allowed to settle for 10 minutes. The mixture was poured through a medium porosity funnel. The tan-pink solids that were retained were washed with 100 mL of ether/hexane (1/2 ratio) and dried in vacuo to provide 5.06 g of tan-pink solids. The clear, nearly colorless filtrate was concentrated to 54 g of a clear pale amber liquid. This material was dissolved in 500 mL of ethyl acetate and washed with 3×50 mL of water. The ethyl acetate solution was dried with magnesium sulfate, filtered, and concentrated to 20.3 g of tan solids. This was combined with the 5.06 g of tan-pink solids from above and purified on a 60 mm id×160 mm silica gel column eluting as follows:
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