Synthesis of N-(6-(3-cyano-4-hydroxyphenyl)pyrimidin-4-yl)cyclopropanecarboxamide

Example 109

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2-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (30 mg, 0.1 mmol) and 2-(methylsulfonyl)ethan-1-ol (13 mg, 0.1 mmol) were dissolved in DMF at room temperature. NaH 60% dispersion in mineral oil (9 mg, 0.21 mmol) was slowly added and then stirred for 24 h. Reaction mixture was diluted with EtOAc and washed with water. Organic layer was dried over MgSO₄ and evaporated under reduced pressure. The crude product was purified via preparative HPLC (5-65% acetonitrile in water, 0.1% trifluoroacteic acid buffer) to yield N-(6-(3-cyano-4-hydroxyphenyl)pyrimidin-4-yl)cyclopropanecarboxamide. LCMS-ESI+ (m/z): [M+H]+ calcd for C₁₅H₁₂N₄O₂: 281.1; found: 281.1.