Reaktion #535854

Reaktionsgleichung

compound

4-Chloro-7-[3,5-bis-O-(2,4-dichlorophenylmethyl)-2-C-methyl-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine

boron trichloride

→

desired compound

Ausbeute 65.6%

4-Chloro-7-(2-C-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

Ausbeute 65.6%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITat −30° C. to −20° C. for 3 h
2. 2
   SonstigeThe reaction was quenched by addition of methanol/dichloromethane (1:1) (90 mL)
3. 3
   workup.STIRRINGthe resulting mixture stirred at −15° C. for 30 min.
4. 4
   Sonstigeneutralized with aqueous ammonia at 0° C.
5. 5
   workup.STIRRINGstirred at room temperature for 15 min
6. 6
   FiltrationThe solid was filtered
7. 7
   Waschenwashed with CH2Cl2/MeOH (1/1, 250 mL)
8. 8
   SonstigeThe combined filtrate was evaporated
9. 9
   Sonstigethe residue was purified by flash chromatography over silica gel

Vorschrift

To a solution of the compound from Step D (5.42 g, 8.8 mmol) in dichloromethane (175 mL) at −78° C. was added boron trichloride (1M in dichloromethane, 88 mL, 88 mmol) 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) (90 mL) and the resulting mixture stirred at −15° C. for 30 min., then neutralized with aqueous ammonia at 0° C. and stirred at room temperature for 15 min. The solid was filtered and washed with CH2Cl2/MeOH (1/1, 250 mL). The combined filtrate was evaporated, and the residue was purified by flash chromatography over silica gel using CH2Cl2 and CH2Cl2:MeOH (99:1, 98:2, 95:5 and 90:10) gradient as the eluent to furnish desired compound (1.73 g) as a colorless foam, which turned into an amorphous solid after treatment with MeCN.

Quelle