反应详情

温度

75 °C

6-bromo-8-cyclopentyl-4-methyl-2-(methylamino)pyrido[2,3-d]pyrimidin-7(8H)-one (375 mg, 1.1 mmole), ethyl acrylate (442 mg, 4.42 mmole), N-cyclohexyl-N-methylcyclohexanamine (280 mg, 1.43 mmole), tri-tert-butylphosphonium tetrafluoroborate (9.61 mg, 0.03 mmole), lithium chloride (42.4 mg, 3.3 mmole), tris(dibenzylideneacetone)dipalladium(0)) (30.3 mg, 0.03 mmole) and 1,4-dioxane (10 ml) were added to a reaction vial equipped with a stir bar. The reaction vial was flushed with nitrogen, capped, and heated at 75° C. for 75 min. The reaction mixture was cooled to ambient temperature, filtered through Celite™, and washed with ethyl acetate. The filtrate and washing were combined, and the volatiles were removed under reduced pressure to a yellow solid residue. This solid residue was crystallized from boiling heptane:ethyl acetate (50 ml: 50 ml). Upon cooling to ambient temperature, needle-liked yellow crystals formed and collected by filtration to give the title compound as a beta-trans isomer (356 mg, 90% yield).

1. customvial equipped with a stir bar
2. customThe reaction
3. customvial was flushed with nitrogen
4. customcapped
5. temperatureThe reaction mixture was cooled to ambient temperature
6. filtrationfiltered through Celite™
7. washwashed with ethyl acetate
8. washThe filtrate and washing
9. customthe volatiles were removed under reduced pressure to a yellow solid residue
10. customThis solid residue was crystallized
11. temperatureUpon cooling to ambient temperature
12. customneedle-liked yellow crystals formed
13. filtrationcollected by filtration