[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([NH:10][C:11]2[CH:12]=[N:13][CH:14]=[N:15][CH:16]=2)[CH:7]=[C:6]([Cl:17])[N:5]=1.[CH3:18]I>C1COCC1.CCOC(C)=O>[Cl:17][C:6]1[CH:7]=[C:8]([N:10]([CH3:18])[C:11]2[CH:16]=[N:15][CH:14]=[N:13][CH:12]=2)[CH:9]=[C:4]([Cl:3])[N:5]=1NaH (103 mg, 4.29 mmol, 1.10 eq) was added to a flame-dried round-bottom flask and anhydrous THF (9.5 mL) was added. The slurry was cooled to 0° C. and compound 13 (938 mg, 3.89 mmol, 1.00 eq) was added as a solution in THF (9.5 mL). After stirring at 0° C. for 30 minutes methyl iodide (267 μL, 4.29 mmol, 1.10 eq) was added and the reaction was allowed to warm to room temperature while stirring overnight. The reaction was diluted with EtOAc and washed with water (1×). The aqueous layer was back extracted (1×) with EtOAc and the combined organics were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 920 mg (93%) of the title compound as a tan solid: 1H NMR (400 MHz, CDCl3) δ 9.14 (s, 1H), 8.87 (s, 2H), 6.77 (s, 2H), 3.36 (s, 3H); [M+1]+: 255.0.
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