Boron Trichloride → (2R,3R,4R,5R)-2-{4-amino-7h-pyrrolo[2,3-d]pyrimidin-7-yl}-3-ethenyl-5-(hydroxymethyl)oxolane-3,4-diol

Temperature

-78 °C

To a solution of the compound from Step C (60 mg) in dichloromethane at −78° C. was added boron trichloride (1M in dichloromethane) dropwise. The mixture was stirred at −78° C. for 2.5 h, then at −30° C. to −20° C. for 3 h. The reaction was quenched by addition of methanol/dichloromethane (1:1) and the resulting mixture stirred at −15° C. for 0.5 h, then neutralized with aqueous ammonia at 0° C. and stirred at room temperature for 15 min. The solid was filtered and washed with methanol/dichloromethane (1:1). The combined filtrate was evaporated and the residue purified by flash chromatography (SiO2, 10% methanol in EtOAc containing 0.1% triethylamine). The fractions containing the product were evaporated to give the title compound as a white solid (10 mg).

1. waitat −30° C. to −20° C. for 3 h
2. customThe reaction was quenched by addition of methanol/dichloromethane (1:1)
3. stirringthe resulting mixture stirred at −15° C. for 0.5 h
4. customneutralized with aqueous ammonia at 0° C.
5. stirringstirred at room temperature for 15 min
6. filtrationThe solid was filtered
7. washwashed with methanol/dichloromethane (1:1)
8. customThe combined filtrate was evaporated
9. customthe residue purified by flash chromatography (SiO2, 10% methanol in EtOAc containing 0.1% triethylamine)
10. additionThe fractions containing the product
11. customwere evaporated

ORD record

ord-949bbf3785544298a982aebe2bcfd131

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08481712B2