反应详情

温度

140 °C

To a solution of 1-[8-chloro-2-(3-methoxyphenyl)imidazo[1,2-α]pyridin-3-yl]-2-propyn-1-one (58 mg, 0.19 mmol) in 1-methyl-2-pyrrolidinone (2 mL) was added N-phenylguanidinium nitrate (185 mg, 0.94 mmol) and potassium carbonate (129 mg, 0.94 mmol). The mixture was heated at 140° C. for 1.25 hours and then cooled to room temperature. Water was added then ether. The organic layer was washed with brine. The aqueous layer was extracted with ether and the combined organics dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (2:1 hexanes-ethyl acetate) provided 4-[8-chloro-2-(3-methoxyphenyl)imidazo[1,2-α]pyridin-3-yl]-N-phenylpyrimidin-2-amine (40 mg, 50%) as a yellow solid. 1H NMR (CDCl3 with 2 drops CD3OD): δ 9.45 (d, 1 H), 8.16 (d, 1 H), 7.60–7.58 (m, 2 H), 7.39 (d, 1 H), 7.34–7.29 (m, 3 H), 7.17–7.15 (m, 2 H), 7.07 (t, 1 H), 6.95 (m, 1 H), 6.75 (t, 1 H), 6.58 (d, 1 H), 3.79 (s, 3 H); MS m/z 428 (M+1).

1. temperaturecooled to room temperature
2. washThe organic layer was washed with brine
3. extractionThe aqueous layer was extracted with ether
4. dry with materialthe combined organics dried over magnesium sulfate
5. filtrationFiltration and concentration