Ammonium Chloride → HCID 59548222, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of N-(5-amino-2-methoxypyridin-3-yl)methanesulfonamide (Step 4, 0.028 g, 0.13 mmol) and 4-(5-chloro-2-fluoropyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (Step 1, 0.0364 g, 0.152 mmol) in DMF (1 mL) in 5 mL microwave vial, NaHMDS (Aldrich, 1 M in THF, 0.52 mL, 0.52 mmol) was added dropwise at 0° C. The solution was stirred at 0° C. for 1.5 h. The reaction mixture was poured into sat'd NH4Cl (15 mL) and stirred. The resulting solid was collected via filtration. The crude product was purified by preparative HPLC (column:Phenomenex, Gemni 5 micron C18 100×30 mm, 10%-90% CH3CN w/0.1% TFA/H2O w/0.1% TFA in 10 min). The corresponding fractions were combined and concentrated. Sat'd NaHCO3 was added to the residue and sonicated. The resulting yellow solid was collected and washed with water and with MeOH to afford 5 N-(5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-chloropyridin-2-ylamino)-2-methoxypyridin-3-yl)methanesulfonamide (12.9 mg, 23% yield) as bright yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.76 (s, 1H) 9.27 (s, 1H) 8.72 (d, J=2.54 Hz, 1H) 8.32 (dd, J=10.47, 2.45 Hz, 2H) 8.09 (d, J=2.15 Hz, 1H) 7.77-8.01 (m, 2H) 3.91 (s, 3H) 3.05 (s, 3H) 2.44 (s, 3H). m/z (ESI, positive ion): 436.9 (M+H)+.

Provenance & Evidence