Ammonium Chloride → N-(5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-methoxypyridin-2-ylamino)-2-chloropyridin-3-yl)methanesulfonamide

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Reaction Steps

To a 5 mL microwave vial, 4-(2-fluoro-5-methoxypyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (0.0550 g, 0.234 mmol) and N-(5-amino-2-chloropyridin-3-yl)methanesulfonamide (Step 2, 0.0579 g, 0.261 mmol) were dissolved into DMF (1 mL). NaHMDS (Aldrich, 1 M in THF, 0.935 mL, 0.935 mmol) was added slowly at 0° C. and the dark red mixture was stirred at that temperature for 40 min. The mixture was poured into sat'd NH4Cl (20 mL) and stirred for 5 min. The resulting solid was collected via filtration, washed with water and purified by preparative HPLC using a Phenomenex Gemni 5 micron C18 100×30 mm column (1%-90% CH3CN w/0.1% TFA/H2O w/0.1% TFA in 10 min). The fractions were combined and concentrated. The residue was taken into sat'd NaHCO3. The aqueous pH was adjusted to pH 4-5 and the resulting solid was collected to give N-(5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-methoxypyridin-2-ylamino)-2-chloropyridin-3-yl)methanesulfonamide (0.0146 g, 14% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.97 (br. s., 1H) 9.62 (br. s., 1H) 8.61 (d, J=14.08 Hz, 2H) 8.41 (br. s., 1H) 8.20 (br. s., 1H) 7.68-8.09 (m, 2H) 3.86 (br. s., 3H) 3.13 (br. s., 3H) 2.45 (br. s., 3H). m/z (ESI, positive ion) m/z: 436.9 (M+H)+.

Provenance & Evidence