Acetone → 4-[2-(methylsulfonyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(3-pyridinyl)-1,3,5-triazin-2-amine

Participants

Reaction Steps

A solution of 0.421 g (1 mmol) of 4-[2-(methylsulfanyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(3-pyridinyl)-1,3,5-triazin-2-amine (from Example 4) in 130 mL acetone and 20 mL HOAc was treated with 1 g KMnO4 in 10 mL water at room temperature. After 30 min, the reaction was decolorized with aq. Na2SO3 solution and the acetone was removed under vacuum. The residue was diluted with water and the pH adjusted to neutral to give a precipitate which was dissolved in CHCl3 and dried. Chromatography on alumina, eluting with CHCl3/EtOAc (9:1) gave 140 mg (31%) of 4-[2-(methylsulfonyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(3-pyridinyl)-1,3,5-triazin-2-amine: mp (MeOH) 208-211° C.; 1H NMR (CDCl3) 8.88 (br s, 1H), 8.38 (dd, J=4.7, 1.4 Hz, 1H), 8.26 (d, J=7.9 Hz, 1H), 8.00 (d, J=7.8 Hz, 1H), 7.77 (dd, J=7.3, 1.2 Hz, 1H), 7.46-7.38 (m, 3H; 2H after D2O exchange), 7.31 (dd, J=8.3, 4.7 Hz, 1H), 4.08 (m, 2H), 3.83 (m, 2H), 3.76 (m, 4H), 3.62 (s, 3H); Anal. Calcd. for C20H20N8O3S 0.5H2O: C, 52.0; H, 4.6; N, 24.3. Found: C, 51.8; H, 4.6; N, 24.3%.

Provenance & Evidence