Hydrogen Peroxide → 4-amino-6-(((1S)-1-(6-fluoro-1-(3-pyridinyl)-1H-benzimidazol-2-yl)ethyl)amino)-5-pyrimidinecarboxamide

Participants

Reaction Conditions

Reaction Steps

To an ice-cooled solution of potassium carbonate (0.027 g, 0.19 mmol) and (S)-4-amino-6-(1-(6-fluoro-1-(pyridin-3-yl)-1H-benzo[d]imidazol-2-yl)ethylamino)pyrimidine-5-carbonitrile (0.060 g, 0.16 mmol) in DMSO (1.60 mL) was added hydrogen peroxide (31.3% in water, 0.078 mL, 0.80 mmol) dropwise under nitrogen atmosphere. The solution was stirred at 0° C. for 1 h then was partitioned between water and EtOAc. Organic extracts were concentrated under reduced pressure then purified by MPLC (eluted with a gradient of 0-10% MeOH in DCM) to afford 4-amino-6-(((1S)-1-(6-fluoro-1-(3-pyridinyl)-1H-benzimidazol-2-yl)ethyl)amino)-5-pyrimidinecarboxamide as an off-white foam. 1H NMR (400 MHz, DMSO-d6) d ppm 1.48 (d, J=6.85 Hz, 3H) 5.26 (quin, J=6.94 Hz, 1H) 6.57 (s, 2H) 6.98 (dd, J=8.90, 2.45 Hz, 1H) 7.14 (ddd, J=9.78, 8.80, 2.54 Hz, 1H) 7.46 (s, 2H) 7.65-7.70 (m, 1H) 7.74 (dd, J=8.80, 4.89 Hz, 1H) 7.77 (s, 1H) 7.94 (d, J=7.63 Hz, 1H) 8.05-8.12 (m, 1H) 8.78 (dd, J=4.79, 1.47 Hz, 1H) 8.82 (d, J=2.15 Hz, 1H). LC-MS (ESI) m/z 393.2 [M+H]+.

Provenance & Evidence