HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2070276Generated: October 31, 2026
Sodium Carbonate → 2-Chloro-4-(pyridin-3-yl)pyrimidine
https://huagongshe.com/reaction/2070276
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2,4-Dichloropyrimidine | HCID 77531 | — |
| Reactant | 3-Pyridinylboronic acid | HCID 2734378 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-Chloro-4-(pyridin-3-yl)pyrimidine | HCID 11805543 | — |
Reaction Steps
Nitrogen was bubbled through a solution of 2,4-dichloropyrimidine (1 eq) in tetrahydrofuran and water (3:1) for 0.5 h. Bis(diphenylphosphino)ferrocene Palladium(II)chloride (0.05 eq) followed by pyridine-3-boronic acid (1 eq) and sodium carbonate (3 eq) was added and the mixture was heated to 60° C. for 16 h under nitrogen. The reaction mixture was concentrated and partitioned between ethyl acetate and water. The organic layer was washed with brine and dried with sodium sulfate and concentrated. Purification on silica gel gave 2-chloro-4-(3-pyridyl)pyrimidine. MS: MH+=190.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08299108B2 |
|---|
| Source dataset | uspto-grants-2012_10 |
|---|
| ORD ID | ord-37032e1efd1e48b6a1d8253a0e6a1795 |
|---|
| Source note | uspto-grants-2012_10 |
|---|
