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

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-4d78fd75a20a402e8af37509a3c481b0

Source dataset

uspto-grants-2004_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06777395B2