HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 446302Generated: October 26, 2026
1,2-Dimethoxyethane → 2-Chloro-4-(2-chloro-pyridin-3-yl)-5-fluoro-pyrimidine
https://huagongshe.com/reaction/446302
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1,2-Dimethoxyethane | HCID 8071 | — |
| Reactant | 2,4-Dichloro-5-fluoropyrimidine | HCID 250705 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | (2-Chloropyridin-3-yl)boronic acid | HCID 2762704 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 2-Chloro-4-(2-chloro-pyridin-3-yl)-5-fluoro-pyrimidine | HCID 77230203 | — |
Reaction Steps
To 2,4-dichloro-5-fluoropyrimidine (500 mg, 2.99 mmol), 2-chloropyridine-3-boronic acid (707 mg, 4.49 mmol), Pd(PPh3)4 (346 mg, 0.30 mmol) was added DME (9.0 mL) and 1 M NaHCO3 (3.0 mL). The mixture was heated overnight in a sealed tube at 80° C., cooled to RT, diluted with EtOAc, and washed with water and saturated Na2CO3. The organic layer was dried over Na2SO4, filtered, concentrated and purified by reverse-phase HPLC to provide 2-chloro-4-(2-chloro-pyridin-3-yl)-5-fluoro-pyrimidine. MS m/z=244, 246 [M]+ and [M+2]+. Calc'd for C9H4Cl2FN3: 244.06.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08476434B2 |
|---|
| Source dataset | uspto-grants-2013_07 |
|---|
| ORD ID | ord-373728d4e35947deb6a1ee43491c8928 |
|---|
| Source note | uspto-grants-2013_07 |
|---|
