HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → HCID 86714515, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | (S)-(-)-N-Boc-prolinol | HCID 643448 | — |
| Reactant | Diisopropyl azodicarboxylate | HCID 5363146 | — |
| Reactant | 6-Chloro-7-iodo-7-deazapurine | HCID 14809281 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86714515 | HCID 86714515 | 77% |
Reaction Steps
To a solution of 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (4.0 g, 14.34 mmol, 1.0 eq), (S)-tert-butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate (4.04 g, 20.08 mmol, 1.4 eq), and PPh3 (7.5 g, 28.68 mmol, 2.0 eq) in dry THF (30 mL), DIAD (5.80 g, 28.68 mmol, 2.0 eq) was added dropwise at 0° C. The mixture was stirred at RT for 5 h. The reaction mixture was concentrated and purified by silica gel chromatography (eluted with PE:EtOAc=1:1) to afford (S)-2-(4-chloro-5-iodo-pyrrolo[2,3-d]pyrimidin-7-ylmethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (5.1 g, 77% in yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08759358B1 |
| Source dataset | uspto-grants-2014_06 |
| ORD ID | ord-68b2951c04834c7eaa59af1cc7d77de0 |
| Source note | uspto-grants-2014_06 |