反应详情

温度

95 °C

A mixture of ethyl 4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (1.00 g, 2.81 mmol), 3-aminophenylboronic acid monohydrate (577 mg, 4.21 mmol), 2 M aqueous sodium carbonate (893 mg, 8.43 mmol), and tetrakis(triphenylphosphine)palladium(0) (649 mg, 0.562 mmol) in dioxane (10 mL) and water (2 mL) was purged with argon. The reaction vessel was sealed in a microwave vial and the reaction mixture heated at 95° C. for 2 hours. The resulting mixture was filtered through Celite. Water (10 mL) was added and the organic layer was separated. The aqueous layer was extracted with ethyl acetate (×3). The combined organic layers were washed with brine (15 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica eluting with 0-100% ethyl acetatehexane to afford ethyl 4-(3-aminophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate. LRMS (ESI) calc'd for C21H29N4O3Si [M+H]+: 413, found 413.

1. customwas purged with argon
2. customThe reaction vessel was sealed in a microwave vial
3. filtrationThe resulting mixture was filtered through Celite
4. additionWater (10 mL) was added
5. customthe organic layer was separated
6. extractionThe aqueous layer was extracted with ethyl acetate (×3)
7. washThe combined organic layers were washed with brine (15 mL)
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customThe residue was purified by chromatography on silica eluting with 0-100% ethyl acetatehexane