HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 2,4-Dimethoxy-5-(6-methyl-pyridin-2-yl)-pyrimidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 2-Bromo-6-methylpyridine | HCID 79205 | — |
| Reactant | (2,4-Dimethoxypyrimidin-5-yl)boronic acid | HCID 2736209 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | 1-Propanol | HCID 1031 | — |
| Product | 2,4-Dimethoxy-5-(6-methyl-pyridin-2-yl)-pyrimidine | HCID 58994162 | 47.7% |
Reaction Steps
2,4-Di-methoxy-pyrimidine-5-boronic acid (500 mg, 2.72 mmol) was dissolved in degassed n-PrOH (40 mL) and then 2-bromo-6-methylpyridine (660 mg, 3.8 mmol), Na2CO3 (865 mg, 8.16 mmol), PPh3 (215 mg, 0.8 mmol) and Pd(OAc)2 (50 mg, 0.22 mmol) were added. The suspension was stirred at reflux for 4 hours. The solvent was evaporated and the crude was partitioned between water and Et2O. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with ethyl acetate-petroleum ether (2-8) to give 300 mg of the title compound (47% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07727988B2 |
| Source dataset | uspto-grants-2010_06 |
| ORD ID | ord-aee16765237f4c5d918624d6c4d3c6ad |
| Source note | uspto-grants-2010_06 |