Sodium Carbonate → 4-(2-Chloro-5-methoxypyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine

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Reaction Conditions

Reaction Steps

1,4-dioxane (10.00 mL) and water (2.5 mL) were added to a stirred mixture of 2-chloro-5-methoxypyridin-3-ylboronic acid (1.03 g, 5.48 mmol), 4-chloro-6-methyl-1,3,5-triazin-2-amine (0.72 g, 4.98 mmol), Na2CO3 (1.32 g, 12.5 mmol), and Pd(PPh3)4 (0.576 g, 0.1 eq) and the mixture was sealed and heated at 90° C. overnight. After cooling, the mixture was concentrated. Flash column chromatographic purification (short column, SiO2, pure DCM to 5% MeOH in DCM) provided 4-(2-chloro-5-methoxypyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (0.644 g, 51%) as a white solid. LCMS (API-ES) m/z 252 (M+H)+; 1H NMR (400 MHz, d6-DMSO) δ 8.24 (d, J=1.17 Hz, 1H) 7.68 (br. s., 2H) 7.65 (d, J=1.17 Hz, 1H) 3.87 (s, 3H) 2.36 (s, 3H).

Provenance & Evidence