反应详情

温度

180 °C

To a suspension of 6-iodo-N,N-dimethyl-1H-indazole-3-carboxamide (100 mg, 0.32 mmol) at 0° C. in DMF (3 mL) was added sodium hydride (19 mg of a 60% dispersion in mineral oil, 0.47 mmol). The reaction mixture was allowed to warm to RT over 15 minutes before the addition of 6-chloro-4-N-methylpyrimidine-2,4-diamine (75 mg, 0.47 mmol). The reaction mixture was then heated at 180° C. for 2 hr. The reaction mixture was allowed to cool to RT. The mixture was cooled to 0° C. and quenched by addition of water (1 mL) and the volatiles evaporated in vacuo. The mixture was diluted with sat ammonium chloride (20 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extracts were dried (Na2SO4), filtered and evaporated in vacuo. Purification of the residue by column chromatography (Biotage, 55-100% ethyl acetate: heptanes) gave the title compound: 1H NMR (500 MHz, DMSO) delta 2.78 (3H, s), 3.08 (3H, s), 3.42 (3H, s), 6.24 (1H, s), 6.48 (2H, s), 7.08 (1H, s), 7.64 (1H, m), 7.79 (1H, m), 9.40 (1H, s); LC-MS: m/z=+438.0 (M+H)+.

1. temperatureto cool to RT
2. temperatureThe mixture was cooled to 0° C.
3. customquenched by addition of water (1 mL)
4. customthe volatiles evaporated in vacuo
5. additionThe mixture was diluted with sat ammonium chloride (20 mL)
6. extractionextracted with ethyl acetate (3×50 mL)
7. dry with materialThe combined organic extracts were dried (Na2SO4)
8. filtrationfiltered
9. customevaporated in vacuo
10. customPurification of the residue by column chromatography (Biotage, 55-100% ethyl acetate: heptanes)