HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 6-(2,4-Dimethoxy-pyrimidin-5-yl)-pyridine-2-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 5-Iodo-2,4-dimethoxypyrimidine | HCID 263416 | — |
| Reactant | 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile | HCID 17750468 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | 1-Propanol | HCID 1031 | — |
| Product | 6-(2,4-Dimethoxy-pyrimidin-5-yl)-pyridine-2-carbonitrile | HCID 58994221 | 44% |
Reaction Steps
5-Iodo-2,4-dimethoxy-pyrimidine (500 mg, 1.88 mmol) was dissolved in degassed n-PrOH (40 ml) and then 6-cyano-pyridine-2-boronic acid pinacol ester (650 mg, 2.82 mmol), Na2CO3 (598 mg, 5.64 mmol), PPh3 (164 mg, 0.62 mmol) and Pd(OAc)2 (42 mg, 0.19 mmol) were added. The suspension was stirred at reflux for 3 hours. The solvent was evaporated and the crude was partitioned between water and ethyl acetate. The organic phase was dried (Na2SO4) and evaporated. The crude was triturated with iPrOH to give 200 mg of the title compound (44% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07727988B2 |
| Source dataset | uspto-grants-2010_06 |
| ORD ID | ord-9c661d50fd2d4b33b0dcf9a476560655 |
| Source note | uspto-grants-2010_06 |