Tetrahydrofuran → Tert-butyl 5-(3-(4-amino-6-methyl-1,3,5-triazin-2-YL)-5-methoxypyridin-2-ylamino)-2-chloropyridin-3-ylcarbamate

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To a 15 mL RB flask was added tert-butyl 5-amino-2-chloropyridin-3-ylcarbamate (0.130 g, 0.533 mmol), 4-(2-fluoro-5-methoxypyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (Example 330 step 5)(0.151 g, 0.640 mmol), and DMF (2.0 mL). The mixture was cooled to 0° C. under N2. Sodium bis(trimethylsilyl)amide, 1.0 m in THF (Aldrich) (2.134 mL, 2.134 mmol) was then added to the solution in one portion. The now burgundy color mixture was stirred at 0° C. for 10 min then warmed up to rt and stirred for 30 min. The reaction mixture was poured into the beaker which had filled with 15 mL sat. NH4Cl. The resulting mixture was stirred at rt for 5 h. The ppt in the solution mixture was collected by filtration. The solid was rinsed with water and dried opened to the air for 4 h. This crude product was purified by column chromatography (40 g, 3% MeOH in DCM) to afford the desired product as a yellow solid (210 mg). MS (ESI pos. ion) m/z: 459.0. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.47 (s, 9H) 2.45 (s, 3H) 3.85 (s, 3H) 7.80 (br. s., 1H) 7.94 (br. s., 1H) 8.20 (d, J=3.07 Hz, 1H) 8.42 (d, J=3.07 Hz, 1H) 8.58 (d, J=2.34 Hz, 1H) 8.63 (d, J=2.34 Hz, 1H) 8.75 (s, 1H) 11.91 (s, 1H).

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