HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 5-(4-Methyl-pyridin-3-yl)-2,4-dimethoxy-pyrimidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 3-Bromo-4-methylpyridine | HCID 817630 | — |
| Reactant | (2,4-Dimethoxypyrimidin-5-yl)boronic acid | HCID 2736209 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | 1-Propanol | HCID 1031 | — |
| Product | 5-(4-Methyl-pyridin-3-yl)-2,4-dimethoxy-pyrimidine | HCID 58994150 | — |
Reaction Steps
2,4-Dimethoxypyrimidine-5-boronic acid (1.3 g, 7.23 mmol) was dissolved in degassed n-PrOH (20 ml) and then 4-methyl-3-bromo-pyridine (830 g, 4.82 mmol), Na2CO3 (1.02 g, 9.64 mmol), PPh3 (126 mg, 0.48 mmol) and Pd(OAc)2 (40 mg) were added. The suspension was stirred at reflux for 3 hours. The solvent was evaporated under vacuum and the crude was partitioned between water and DCM. The organic phase was dried (Na2SO4) and evaporated to give the title compound that was used without further purification in the next step (quantitative yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07727988B2 |
| Source dataset | uspto-grants-2010_06 |
| ORD ID | ord-a66b7a3b045043e6b8987f76f458da43 |
| Source note | uspto-grants-2010_06 |