[C:1]([C:3]1[C:8](F)=[CH:7][C:6]([C:10]2[CH:15]=[C:14](C)[N:13]=[C:12]([NH:17]C(=O)C)[N:11]=2)=[CH:5][C:4]=1F)#[N:2].[H-].[Na+].O.[NH2:25][NH2:26].O.CN([CH:31]=[O:32])C>CCO>[NH2:17][C:12]1[N:11]=[C:10]([C:6]2[CH:5]=[C:4]3[C:3]([C:1]([NH2:2])=[N:25][NH:26]3)=[C:8]([O:32][CH3:31])[CH:7]=2)[CH:15]=[CH:14][N:13]=1To a solution of N-[4-(4-cyano-3,5-difluorophenyl)-6-methyl-2-pyrimidinyl]acetamide in DMF (3 mL) was added sodium hydride (1.5 eq.). To the basic solution was added dropwise a solution of the appropriate alcohol (1 eq.) and sodium hydride (1 eq.) in DMF (3 mL). The vial that contained the alkoxide solution was rinsed with more DMF (1 mL). When the reaction was judged complete (HPLC, ˜1 hour), the reaction mixture was poured onto saturated aqueous ammonium chloride. After standing for ˜10-15 minutes, the precipitate formed was collected by vacuum filtration. To the resulting solid in EtOH was added hydrazine monohydrate (50 eq.), and the reaction mixture was stirred overnight at 90° C. The reaction was poured onto EtOAc and water. The organic phase was separated and the aqueous layer was further extracted with EtOAc. The combined organic layers were concentrated. Work-up from here varies according to the compound.
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