HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 136068436, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | (2-Hydroxyphenyl)boronic acid | HCID 2773454 | — |
| Reactant | HCID 58394337 | HCID 58394337 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 136068436 | HCID 136068436 | 89% |
Reaction Steps
A mixture of (S)-tert-butyl 3-(2-chloro-5-phenylpyrimidin-4-ylamino)pyrrolidine-1-carboxylate (0.153 g, 0.408 mmol), 2-hydroxyphenylboronic acid (0.169 g, 1.24 mmol), palladium catalyst (0.013 g, 0.020 mmol) and 1 M aqueous Na2CO3 (0.82 mL, 0.82 mmol) in DME (4 mL) was refluxed for 24 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 (0.156 g, 89%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08324226B2 |
| Source dataset | uspto-grants-2012_12 |
| ORD ID | ord-f3da3bb1066140859a5c0acff2ddf49e |
| Source note | uspto-grants-2012_12 |