反应详情

To a stirred solution of 2-chloro-6-(p-methoxybenzylamino)-4-pyridine-methanol (278 mg, 1 mmol) in chloroform (10 ml) at 0° C. (ice bath), was added triethylamine (210 μl, 1.5 mmol) followed by methanesulfonyl chloride (90 μl, 1.2 mmol). After stirring for 1.5 hr., the mixture was diluted with dichloromethane, washed with aqueous saturated sodium bicarbonate solution, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was further dried in high vacuo and mixed with 3-[3-(5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile (98) (323 mg, 1 mmol), anhydrous powdered potassium carbonate (138 mg, 1 mmol), lithium iodide (134 mg, 1 mmol). Anhydrous DMF (5 ml) was then added into the mixture and stirred for overnight at room temperature. The mixture was evaporated in vacuo. The residue was dissolved in methanol-dichloromethane (1:9), filtered through celite pad, and evaporated in vacuo to give a light yellow foam. The crude product was purified by silica gel column chromatography (eluent, EA:hexanes (1:2); The fraction of Rf=0.19 was collected.) to afford 323 mg (55%) of a pale yellow foam.

1. washwashed with aqueous saturated sodium bicarbonate solution
2. dry with materialdried with anhydrous magnesium sulfate
3. filtrationfiltered
4. customevaporated in vacuo
5. customThe residue was further dried in high vacuo
6. stirringstirred for overnight at room temperature
7. customThe mixture was evaporated in vacuo
8. dissolutionThe residue was dissolved in methanol-dichloromethane (1:9)
9. filtrationfiltered through celite pad
10. customevaporated in vacuo
11. customto give a light yellow foam
12. customThe crude product was purified by silica gel column chromatography (eluent, EA:hexanes (1:2)
13. customThe fraction of Rf=0.19 was collected