4-Chloro-6-methyl-1,3,5-triazin-2-amine → 4-(2-Fluoro-5-methylpyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine

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Reaction Conditions

Reaction Steps

1,4-Dioxane (3.00 mL, 8.5 mmol) was added to a mixture of bis(di-tert-butyl (4-dimethylaminophenyl)phosphine)dichloropalladium(II) (Aldrich, St. Louis, Mo.) (0.27 g, 0.43 mmol), 2-fluoro-5-methylpyridin-3-ylboronic acid (1.6 g, 10 mmol), 4-chloro-6-methyl-1,3,5-triazin-2-amine (1.24 g, 8.5 mmol) and potassium acetate (2.5 g, 26 mmol) and the mixture was sealed and heated at 120° C. for 30 min under microwave irradiation. After cooling, the mixture was passed through a short plug of Celite® (diatomaceous earth). The filter cake was washed with DCM (3×20 mL). The combined organic phases were concentrated. Flash column chromatographic purification (short column, SiO2, pure DCM to 5% MeOH in DCM) provided 4-(2-fluoro-5-methylpyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (0.76, 41%) as a white solid which was used for the next step. LCMS (API-ES) m/z 220 (M+H)+.

Provenance & Evidence