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4-(6-fluoro-5-methylpyridin-3-yl)-6-methylpyrimidine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
52%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,4-dioxane; at 80℃; for 3.0h;
To a solution of <strong>[904326-92-7]2-fluoro-3-methylpyridine-5-boronic acid</strong> (0.048 g, 0.311 mmol) in 1,4-dioxane (3 mL), 4-chloro-6-methylpyrimidine (0.04 g, 0.311 mmol) was added PdCl2(dppf)-CH2Cl2 adduct (0.025 g, 0.031 mmol) and CS2CO3 (0.304 g, 0.933 mmol). The reaction mixture was heated at 80 C for 3 h. The reaction mixture was cooled to room temperature then filtered through diatomaceous earth (Celite), washing the bed with ethyl acetate (100 mL). The filtrate was concentrated under reduced pressure to afford 4-(6-fluoro-5-methylpyridin-3-yl)-6- methylpyrimidine (0.04 g, 0.160 mmol, 52% yield) as a brown solid. LCMS (ESI) m/e 204.2 [(M+H) +, calcd for C11H11FN3 204.1]; LC/MS retention time (Method Al): to = 2.30 min.
4-(5-chloro-6-fluoropyridin-3-yl)-6-methylpyrimidine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
29%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,4-dioxane; at 80℃; for 3.0h;
A mixture of <strong>[1366482-32-7](5-chloro-6-fluoropyridin-3-yl)boronic acid</strong> (0.055 g, 0.311 mmol), 4-chloro-6-methylpyrimidine (0.04 g, 0.311 mmol), PdCl2(dppf)-CH2Cl2 adduct (0.025 g, 0.031 mmol) and Cs2C03 (0.304 g, 0.933 mmol) in 1,4-dioxane (3 mL) was heated at 80 C for 3 h. The reaction mixture was cooled to room temperature then filtered through diatomaceous earth (Celite), washing the bed with ethyl acetate (100 mL). The filtrate was concentrated under reduced pressure to afford 4-(5-chloro-6-fluoropyridin-3-yl)-6-methylpyrimidine (0.035 g, 0.090 mmol, 29% yield) as a brown solid. LCMS (ESI) m/e 224.5 [(M+H) +, calcd for CioH8ClFN3 224.0]; LC/MS retention time (method B): = 0.86 min.
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