Tetrahydrofuran → HCID 59548471, compound

Participants

Reaction Conditions

Reaction Steps

To a 15 mL RB flask was added N-(5-amino-2-chloropyridin-3-yl)cyclopropanesulfonamide (0.050 g, 0.202 mmol), 4-(2-fluoropyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (0.050 g, 0.242 mmol), and DMF (2.0 mL). The mixture was cooled to 0° C. under N2. Sodium bis(trimethylsilyl)amide, 1.0 m solution in THF (Aldrich) (0.807 mL, 0.807 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 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 15 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 (60.0 mg). MS (ESI pos. ion) m/z: 433.0. 1H NMR (300 MHz, CDCl3) δ ppm 0.97-1.14 (m, 2H) 1.33 (dd, J=4.60, 1.83 Hz, 2H) 2.51-2.69 (m, 4H) 5.42 (br. s., 2H) 6.75 (s, 1H) 6.92 (dd, J=7.82, 4.90 Hz, 1H) 8.32-8.45 (m, 1H) 8.56 (d, J=2.34 Hz, 1H) 8.76 (d, J=2.34 Hz, 1H) 8.87 (dd, J=7.89, 1.75 Hz, 1H) 12.36 (s, 1H).

Provenance & Evidence