Potassium Carbonate → 2-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-5-nitro-N-(3-pyridinyl)-4-pyrimidinamine

Participants

Reaction Conditions

Reaction Steps

A mixture of 0.23 g of the above nitro compound (0.68 mmol), 0.147 g (0.74 mmol) of 2-difluoromethyl-4-methoxy-1H-benzimidazole (Example 2) and 0.38 g (2.75 mmol) of powdered K2CO3 in 4 mL of DMSO was heated at 120° C. for 4 hrs. The reaction mixture was diluted with water, and extracted with EtOAc (×4). The combined organic layers were washed with brine, dried, and concentrated. The residue was purified by chromatography on silica, eluting first with hexanes/EtOAc (1:1), and then with CH2Cl2/EtOAc (2:1), to give 0.253 g (75% yield) of 2-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-5-nitro-N-(3-pyridinyl)-4-pyrimidinamine, as a yellow powder: 1H NMR (CDCl3) δ 10.26 (s, 1H), 8.72 (d, J=2.4 Hz, 1H), 8.60 (dd, J=4.8, 1.4 Hz, 1H), 7.95 (ddd, J=8.3, 2.4, 1.6 Hz, 1H), 7.45 (dd, J=8.3, 0.6 Hz, 1H), 7.40 (dd, J=8.3, 4.8 Hz, 1H), 7.18 (t, J=8.3 Hz, 1H), 7.11 (t, JHF=53.5 Hz, 1H), 6.78 (d, J=7.8 Hz, 1H), 4.03 (s, 3H), 3.88 (t, J=4.5 Hz, 4H), 3.70 (t, J=4.5 Hz, 4H).

Provenance & Evidence