HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 5-(2-Fluoro-5-methylpyridin-3-yl)-2,4-dimethoxy-pyrimidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | (2,4-Dimethoxypyrimidin-5-yl)boronic acid | HCID 2736209 | — |
| Reactant | 3-Bromo-2-fluoro-5-methylpyridine | HCID 21816563 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | 1-Propanol | HCID 1031 | — |
| Product | 5-(2-Fluoro-5-methylpyridin-3-yl)-2,4-dimethoxy-pyrimidine | HCID 58994169 | 33.4% |
Reaction Steps
2,4-Dimethoxy-pyrimidine-5-boronic acid (842 mg, 4.60 mmol) was dissolved in degassed n-PrOH (55 ml) and then 2-fluoro-3-bromo-5-methylpyridine (800 mg, 4.21 mmol), Na2CO3 (1.46 g, 13.77 mmol), PPh3 (348 mg, 1.33 mmol) and Pd(OAc)2 (101 mg, 0.45 mmol) were added. The suspension was stirred at reflux for 2 hours. After cooling, the solvent was evaporated under vacuum and the crude was partitioned between water and ethyl acetate. The organic phase was dried (Na2SO4) and evaporated. The residue was triturated with Et2O to give 350 mg of the title compound as a gray powder (31% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07727988B2 |
| Source dataset | uspto-grants-2010_06 |
| ORD ID | ord-12f4a5822159455fbcc84489de49ee47 |
| Source note | uspto-grants-2010_06 |