Boron Trichloride → (2R,3R,4R,5R)-2-(2-amino-4-chloropyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)-3-methyloxolane-3,4-diol

Temperatur

-78 °C

To a solution of the product from Step A (630 mg, 1.0 mmol) in CH2Cl2 (20 mL) at −78° C. was added boron trichloride (1M in CH2Cl2) (10 mL, 10 mmol). The mixture was stirred at −78° C. for 2 h, then at −20° C. for 2.5 h. The reaction was quenched with CH2Cl2/MeOH (1:1) (10 mL), stirred at −20° C. for 0.5 h, and neutralized at 0° C. with aqueous ammonia. The solid was filtered, washed with CH2Cl2/MeOH (1:1) and the combined filtrate evaporated in vacuo. The residue was purified on a silica gel column with CH2Cl2/MeOH, 50/1 and 20/1 as eluent to give the title compound as a colorless foam (250 mg).

1. waitat −20° C. for 2.5 h
2. customThe reaction was quenched with CH2Cl2/MeOH (1:1) (10 mL)
3. stirringstirred at −20° C. for 0.5 h
4. customneutralized at 0° C. with aqueous ammonia
5. filtrationThe solid was filtered
6. washwashed with CH2Cl2/MeOH (1:1)
7. customthe combined filtrate evaporated in vacuo
8. customThe residue was purified on a silica gel column with CH2Cl2/MeOH, 50/1 and 20/1 as eluent

ORD-Eintrag

ord-fa3ee95cfef74924b60fffe0115dadc0

Quelldatensatz

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08481712B2