Water → Racemic 1-{4-[5-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-ethane-1,2-diol

Participants

Reaction Steps

To a solution of isopropyl-{4-methyl-6-[3-(4-vinyl-phenyl)-[1,2,4]oxadiazol-5-yl]-pyrimidin-2-yl}-amine (Intermediate 8: 2.78 g, 8.67 mmol) in acetone (45 mL) are added water (4 mL) and a 2.5% aq. solution of OsO4 (136 μL), followed by N-methyl-morpholine-N-oxide monohydrate (1.4 g, 10.4 mmol). The reaction mixture is stirred at rt for 18 h. Another 68 μL of 2.5% aq. solution of OsO4 is added and stirring is continued for another 3 h. The mixture is then diluted with DCM (150 mL), and washed with water (3×50 mL), dried over MgSO4, filtered and evaporated to give 0.97 g of racemic 1-{4-[5-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-ethane-1,2-diol as a brown solid; LC-MS: tR=0.84 min; [M+H]+=356.04. 1H NMR (CDCl3) δ 1.30 (d, J=6.5 Hz, 6H), 2.16 (s br, 1H), 2.49 (s, 3H), 2.74 (s br, 1H), 3.72 (dd, J=11.0, 8.0 Hz, 1H), 3.86 (dd, J=11.0, 3.3 Hz, 0H), 4.31 (m, 1H), 4.94 (dd, J=7.8, 3.3 Hz, 1H), 5.28 (s br, 1H), 7.30 (s, 1H), 7.55 (d, J=8.3 Hz, 2H), 8.20 (d, J=8.3 Hz, 2H).

Provenance & Evidence