HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 58394337, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Phenylboronic Acid | HCID 66827 | — |
| Reactant | HCID 58394392 | HCID 58394392 | — |
| Catalyst | Palladium Chloride | HCID 24290 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 58394337 | HCID 58394337 | 82% |
Reaction Steps
A mixture of (S)-tert-butyl 3-(5-bromo-2-chloropyrimidin-4-ylamino)pyrrolidine-1-carboxylate (0.200 g, 0.539 mmol), phenylboronic acid (0.077 g, 0.636 mmol), PdCl2.dPPf (0.019 g, 0.026 mmol) and 1 M aqueous Na2CO3 (1.06 mL, 1.06 mmol) in DME (5.3 mL) was refluxed for 16 hours. After cooling, water (50 mL) was added and the aqueous phase was extracted with diethyl ether (3×50 mL). The combined organic extracts were dried (MgSO4) and concentrated. The crude product was purified by silica gel chromatography (40% ethyl acetate/hexanes) to give the title compound as an oil (0.163 g, 82%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08324226B2 |
| Source dataset | uspto-grants-2012_12 |
| ORD ID | ord-48674ecd660346ed972a42e2c62b7ae9 |
| Source note | uspto-grants-2012_12 |