Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 2-Fluoro-4-nitrophenol | HCID 9825 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4,6-Dichloropyrimidine | HCID 70943 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 59853028 | HCID 59853028 | 96.4% |
Reaction Steps
A mixture of 4,6-dichloropyrimidine (Aldrich, 0.74 g, 5.0 mmol), 2-fluoro-4-nitrophenol (Aldrich, 0.79 g, 5.0 mmol) and DMF (10 ml) was treated with potassium carbonate (0.72 g, 5.2 mmol) and heated at 80° C. for 3 h. The mixture was cooled, diluted with water and extracted with ethyl acetate. The ethyl acetate extract was washed with brine, dried (MgSO4), and concentrated to give the crude product as a yellow solid. The crude product was triturated with isopropyl ether to give 4-chloro-6-(2-fluoro-4-nitrophenoxy)pyrimidine as a yellow solid (1.3 g, 94%). 1H NMR (DMSO-d6) δ 8.80 (s, 1H), 8.51 (dd, 1H, J=8.6, 2.5 Hz), 8.31 (d, 1H, J=9.1 Hz), 7.87 (d, 1H, J=9.1 Hz), 7.84 (s, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07459562B2 |
|---|
| Source dataset | uspto-grants-2008_12 |
|---|
| ORD ID | ord-77656f45a03548a391cd59615f2d333a |
|---|
| Source note | uspto-grants-2008_12 |
|---|