HuagongsheHuagongshe Chemistry Print Report · For research reference only
(2R,3R,4R,5R)-2-(2-amino-4-chloropyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)-3-methyloxolane-3,4-diol → 7-(2-C-Methyl-b-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (2R,3R,4R,5R)-2-(2-amino-4-chloropyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)-3-methyloxolane-3,4-diol | HCID 11483860 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Product | 7-(2-C-Methyl-b-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine | HCID 9878801 | 81.6% |
Reaction Steps
A mixture of 2-amino-4-chloro-7-(2-C-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-c]pyrimidine (Example 118, Step B) (20 mg, 0.07 mmol) in EtOH (1.0 mL), pyridine (0.1 mL) and 10% Pd/C (6 mg) under H2 (atmospheric pressure) was stirred overnight at room temperature. The mixture was filtered through a Celite pad which was thoroughly washed with EtOH. The combined filtrate was evaporated and purified on a silica gel column with CH2Cl2/MeOH, 20/1 and 10/1, as eluent to give the title compound as a white solid (16 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08481712B2 |
| Source dataset | uspto-grants-2013_07 |
| ORD ID | ord-3725008e87964f10a1bd96f39bcd8d76 |
| Source note | uspto-grants-2013_07 |