Dimethyl Sulfoxide → Isopropyl 4-(6-(2,4-dimethyl-6-(methylsulfonyl)pyridin-3-ylamino)-5-methoxypyrimidin-4-yloxy)piperidine-1-carboxy-late

Participants

Reaction Conditions

Reaction Steps

To a solution of isopropyl 4-(6-(6-bromo-2,4-dimethylpyridin-3-ylamino)-5-methoxypyrimidin-4-yloxy)piperidine-1-carboxylate (500 mg, 1.0 mmol) in 10 ml of DMSO, were added sodium sulfinate (0.36 g, 3.5 mmol), (CuOTf)2PhH (0.051 g, 0.10 mmol), and N,N′-dimethylethylamine (0.018 g, 0.20 mmol) at an ambient temperature. The reaction was heated to 150° C. for 8 hrs. The reaction was cooled to room temperature and poured into H2O. The organics were extracted with ethyl acetate and dried over MgSO4. The ethyl acetate was concentrated under vacuum and purified over SiO2 to afford isopropyl 4-(6-(2,4-dimethyl-6-(methylsulfonyl)pyridin-3-ylamino)-5-methoxypyrimidin-4-yloxy)piperidine-1-carboxy-late. 1HNMR (CDCl3, 400 MHz) δ 1.24 (d, J=1.6 Hz, 6H), 1.75-1.81 (m, 2H), 1.98-2.02 (m, 2H), 2.25 (s, 3H), 2.65 (s, 3H), 3.21 (s, 3H), 3.52-3.65 (m, 2H), 3.65-3.75 (m, 1H), 3.84 (s, 3H), 5.21-5.35 (m, 1H), 7.78 (s, 1H), 7.79 (s, 1H), 8.89 (s, 1H). Exact mass calculated for C22H31N5O6S 493.58 found 494.5 (MH+).

Provenance & Evidence