Sodium Carbonate → N-[3-(2-aminopyridin-4-yl)-5-methylphenyl]-4-methoxypyrimidin-2-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of N-(3-bromo-5-methylphenyl)-4-methoxypyrimidin-2-amine (125 mg, 0.425 mmol), 2-aminopyridine-4-boronic acid (103 mg, 0.467 mmol), PdCl2(dppf)-CH2Cl2 adduct (35 mg, 0.042 mmol) and sodium carbonate (425 μL, 0.850 mmol) in dioxane (3 mL) was heated to 100° C. for 14 hours. The reaction mixture was filtered through a CELITE pad and washed with dioxane (3×). The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography (methanol/ethyl acetate) to give N-[3-(2-aminopyridin-4-yl)-5-methylphenyl]-4-methoxypyrimidin-2-amine as a tan solid. MS ESI calc'd for C17H18N5O [M+H]+ 308. found 308. 1H NMR (500 MHz, DMSO-d6) δ 9.59 (s, 1H), 8.20 (d, J=5.7 Hz, 1H), 7.95-7.88 (m, 2H), 7.61 (s, 1H), 7.00 (s, 1H), 6.69 (d, J=5.4 Hz, 1H), 6.64 (s, 1H), 6.28 (d, J=5.6 Hz, 1H), 5.95 (s, 2H), 3.92 (s, 3H), 2.32 (s, 3H).

Provenance & Evidence