HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 5-(6-Chloro-pyridin-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 | 2-Chloro-5-iodopyridine | HCID 4397176 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | 1-Propanol | HCID 1031 | — |
| Product | 5-(6-Chloro-pyridin-3-yl)-2,4-dimethoxy-pyrimidine | HCID 58994225 | — |
Reaction Steps
2,4-Dimethoxy-pyrimidine-5-boronic acid (1.14 g, 6.26 mmol) was dissolved in degassed n-PrOH (20 ml) and then 2-chloro-5-iodopyridine (1 g, 4.2 mmol), Na2CO3 (884 mg, 15.8 mmol), PPh3 (109 mg, 0.42 mmol) and Pd(OAc)2 (46 mg) were added. The suspension was stirred at reflux for 2.5 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 in the next step without further purification (quantitative yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07727988B2 |
| Source dataset | uspto-grants-2010_06 |
| ORD ID | ord-83a8359273f84a0e9c3c5ff492ad4420 |
| Source note | uspto-grants-2010_06 |