Sodium hydride → 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo(2,3-d)pyrimidine

Temperature

0 °C

To a stirred suspension of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (3.00 g, 19.5 mmol) in DMF (45 mL) was added SEM-Cl (5.20 mL, 29.3 mmol). The resulting mixture was placed under nitrogen and cooled to 0° C. in an ice bath. NaH (0.938 g of a 60% dispersion in mineral oil, 23.4 mmol) was added, the resulting yellow suspension was stirred at 0° C. for approximately 1 hour. The reaction was quenched with 10% aqueous NaCl (180 mL), and the resulting mixture was extracted with EtOAc (180 mL). The organic washings were washed with additional 10% aqueous NaCl (180 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to a crude oil. The oil was purified by column chromatography on silica gel eluting with EtOAc/hexane (2-20%) to afford the title compound as an oil. LRMS calc'd for C12H19ClN3OSi [M+H]+, 284; found 284. 1H NMR (500 MHz, CDCl3) δ 8.67 (s, 1H), 7.39 (d, 1H), 6.67 (d, 1H), 5.65 (s, 2H), 3.52 (t, 2H), 0.91 (t, 2H), 0.06 (s, 9H).

1. customThe reaction was quenched with 10% aqueous NaCl (180 mL)
2. extractionthe resulting mixture was extracted with EtOAc (180 mL)
3. washThe organic washings were washed with additional 10% aqueous NaCl (180 mL)
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo to a crude oil
7. customThe oil was purified by column chromatography on silica gel eluting with EtOAc/hexane (2-20%)

ORD record

ord-0f9337b5adf14ed08c8028f6a23ae11a

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08937077B2