Boron Trichloride → 4-Chloro-7-(2-C-ethyl-beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

Temperature

-78 °C

To a solution of the compound from Step B (307 mg, 0.45 mmol) in dichloromethane (8 mL) was added boron trichloride (1M in dichloromethane) (4.50 mL, 4.50 mmol) at −78° C. The mixture was stirred at −78° C. for 1 h, then at −10° C. for 3 h. The reaction was quenched by addition of methanol/dichloromethane (1:1) (10 mL), stirred at −15° C. for 30 min, and neutralized by addition of aqueous ammonium hydroxide. The mixture was evaporated in vacuo and the resulting oil purified on silica gel using methanol/dichloromethane (1:9) as eluent. Fractions containing the product were pooled and evaporated in vacuo to give the desired product (112 mg) as a colorless foam.

1. waitat −10° C. for 3 h
2. customThe reaction was quenched by addition of methanol/dichloromethane (1:1) (10 mL)
3. stirringstirred at −15° C. for 30 min
4. additionneutralized by addition of aqueous ammonium hydroxide
5. customThe mixture was evaporated in vacuo
6. customthe resulting oil purified on silica gel
7. additionFractions containing the product
8. customevaporated in vacuo

ORD record

ord-28cfee93d9c546ab919be708a08822e5

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07105499B2