[H-].[Na+].F[C:4]1[C:5](/[C:17](/[C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[N:18]\[OH:19])=[N:6][CH:7]=[CH:8][C:9]=1[C:10]1[C:11]([OH:16])=[N:12][CH:13]=[N:14][CH:15]=1>C1COCC1.CN(C=O)C.C(Cl)Cl>[F:26][C:23]1[CH:24]=[CH:25][C:20]([C:17]2[C:5]3=[N:6][CH:7]=[CH:8][C:9]([C:10]4[C:11]([OH:16])=[N:12][CH:13]=[N:14][CH:15]=4)=[C:4]3[O:19][N:18]=2)=[CH:21][CH:22]=1To a suspension of sodium hydride (0.030 g, 0.742 mmol) in THF (Ratio: 1.8, Volume: 2.272 ml) was added dropwise (Z)-(3-fluoro-4-(4-hydroxypyrimidin-5-yl)pyridin-2-yl)(4-fluorophenyl)methanone oxime (0.116 g, 0.353 mmol) in DMF (Ratio: 1.0, Volume: 1.262 ml) slowly. The reaction mixture was heated at 70° C. for 3.5 hr. Additional NaH (12 mg) was added. The reaction mixture was heated at 70° C. for 2.5 hr, and then allowed to cool to room temperature. The solvent was evaporated, and the mixture was further concentrated in vacuo to afford a brown residue. The crude material was dissolved in a minimal amount of CH2Cl2 to be chromatographed (required a few drops of MeOH). Purification of the crude material by silica gel chromatography using an ISCO machine (24 g column, 35 mL/min, 0-30% MeOH in CH2Cl2 over 25 min, tr=9 min) gave the title compound (53.4 mg, 0.173 mmol, 49.0% yield) as a yellow solid. ESI MS (M+H)+=309.1.
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