Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 5-Bromopyrimidine | HCID 78344 | — |
| Reactant | Tert-butyl [(1S)-1-(3-hydroxyphenyl)ethyl]carbamate | HCID 56971802 | — |
| Catalyst | Copper iodide | HCID 83717 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 60004112 | HCID 60004112 | 89.6% |
Reaction Steps
A mixture of (S)-[1-(3-hydroxy-phenyl)-ethyl]-carbamic acid tert-butyl ester (1 g, 4.2 mmol), 5-bromo-pyrimidine (0.8 g, 5.1 mmol), potassium carbonate (powder, 1.4 g, 10.1 mmol), copper iodide (325 mesh powder, 0.6 g, 3.2 mmol) and pyridine (5 mL) was heated at 115° C. for 24 h. CH2Cl2 (100 mL) was added, the reaction mixture was filtered through celite, rinsed with CH2Cl2 (2×50 mL), and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with 1:1/Hexane:EtOAc to give the title product (0.81 g, 61% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06900210B2 |
|---|
| Source dataset | uspto-grants-2005_05 |
|---|
| ORD ID | ord-76947cb7044f444ebb8c566b9a136d1b |
|---|
| Source note | uspto-grants-2005_05 |
|---|
