Tetrahydrofuran → N-(5-(3-(4-Amino-6-methyl-1,3,5-triazin-2-YL)-5-(1-morpholinoethyl)pyridin-2-ylamino)-2-chloropyridin-3-YL)methanesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a 15 mL round-bottom flask was added 4-(2-fluoro-5-(1-morpholinoethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (0.100 g, 0.314 mmol), N-(5-amino-2-chloropyridin-3-yl)methanesulfonamide (0.084 g, 0.377 mmol), and DMF (2.0 mL). The mixture was cooled to 0° C. under N2. Sodium bis(trimethylsilyl)amide, 1.0 m in THF (0.254 mL, 1.256 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 stir for 1 h. The reaction mixture was extracted with EtOAc (2×10 mL), CHCl3 (2×10 mL). The combined organic layer were dried over MgSO4 and concentrated. The crude product was purified by column chromatography (40 g, 3% MeOH in DCM) to afford the desired product as a yellow solid (100 mg). MS (ESI pos. ion) m/z: 520.1. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.34 (d, J=6.58 Hz, 3H) 2.33 (br. s., 2H) 2.46 (s, 5H) 3.13 (s, 3H) 3.46 (d, J=4.82 Hz, 1H) 3.57 (br. s., 4H) 7.69-8.00 (m, 2H) 8.32 (s, 1H) 8.66 (d, J=2.48 Hz, 2H) 8.74 (s, 1H) 9.65 (br. s., 1H).

Provenance & Evidence