Sodium hydride → ethyl 4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

To a solution of ethyl 4-(3-nitrophenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (2.0 g, 6.4 mmol) in THF (30 mL), was added sodium hydride (180 mg, 7.50 mmol) at 0° C. The reaction was stirred for 1 hour at room temperature, then cooled back to 0° C., followed by the dropwise addition of SEMCl (1.28 g, 7.68 mmol). The solution was stirred for 4 hours at room temperature before being quenched by addition of 50 mL of a water/ice mixture. The resulting mixture was concentrated in vacuo, and the resulting solution was extracted with ethyl acetate (×3). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The reaction was then purified by chromatography using silica gel, eluting with 1-50% EtOAc/petroleum ether. The product was collected and concentrated in vacuo to afford ethyl 4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate as a yellow oil. LRMS (ESI) calc'd for C21H27N4O5Si [M+H]+: 443, found 443.

1. temperaturecooled back to 0° C.
2. stirringThe solution was stirred for 4 hours at room temperature
3. custombefore being quenched by addition of 50 mL of a water/ice mixture
4. concentrationThe resulting mixture was concentrated in vacuo
5. extractionthe resulting solution was extracted with ethyl acetate (×3)
6. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe reaction was then purified by chromatography
10. washeluting with 1-50% EtOAc/petroleum ether
11. customThe product was collected
12. concentrationconcentrated in vacuo

ORD record

ord-6d43b0b0bf4f4981aa2f2d6de6fe31df

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08993756B2