m-Chloroperbenzoic acid → 3-(((3R,4R)-3-aminotetrahydro-2H-pyran-4-yl)amino)-5-(p-tolylamino)-1,2,4-triazine-6-carboxamide

Beteiligte Stoffe

Reaktionsschritte

3-(Methylthio)-5-(p-tolylamino)-1,2,4-triazine-6-carboxamide (26 mg, 0.095 mmol) was dissolved in 4 mL NMP. To it was added mCPBA (77%) (86 mg, 0.38 mmol). The mixture was stirred at RT for 1 h. To it was added DIEA (0.17 mL, 0.95 mmol) and tert-butyl((3R,4R)-4-aminotetrahydro-2H-pyran-3-yl)carbamate (41 mg, 0.19 mmol). The mixture was stirred at 80° C. for 2 h. The mixture was diluted with 100 mL EtOAc, washed with 1N NaOH and brine, dried, concentrated in vacuo. It was then treated with neat TFA for 1 h at RT. The mixture was diluted with water and subjected to reverse phase preparative HPLC to isolate the title compound (27 mg) as HCl salt. MS found for C16H21N7O2 as (M+H)+ 344.4. UV: λ=235, 273 nm. Proton NMR: (CD3OD) δ 7.56 (2H, d, J=6.8 Hz), 7.31 (2H, d, J=7.6 Hz), 4.36 (1H, dt, J=11.6; 5.2 Hz), 4.10 (1H, dd, J=11.6; 4.8 Hz), 3.99 (1H, d, J=13.2 Hz), 3.74 (1H, s), 3.67-3.61 (2H, m), 2.38 (3H, s), 2.16 (1H, m), 1.91 (1H, m) ppm.

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