HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → 2-(6-((2-(3-Chlorophenyl)-6-ethylpyrimidin-4-yl)oxy)pyridin-3-yl)acetonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4-Chloro-2-(3-chlorophenyl)-6-ethylpyrimidine | HCID 43557580 | — |
| Reactant | 2-(6-Oxo-1,6-dihydropyridin-3-yl)acetonitrile | HCID 83350258 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-(6-((2-(3-Chlorophenyl)-6-ethylpyrimidin-4-yl)oxy)pyridin-3-yl)acetonitrile | HCID 90111123 | 22% |
Reaction Steps
A solution of 4-chloro-2-(3-chlorophenyl)-6-ethylpyrimidine (0.300 g, 1.19 mmol), 2-(6-oxo-1,6-dihydropyridin-3-yl)acetonitrile (0.239 g, 1.78 mmol), and potassium carbonate (0.246 g, 1.78 mmol) in DMF (3 mL) was heated with microwave irradiation to 120° C. for 1 h. After this time, the reaction was cooled and concentrated. The residue was purified by preparative HPLC (water/acetonitrile with 0.05% TFA) to afford the title compound (0.066 g, 22%). MW=350.80. 1H NMR (CD3OD, 300 MHz) δ 8.51-8.41 (m, 2H), 8.32-8.28 (m, 1H), 7.89 (s, 1H), 7.64 (dd, J1=12.1 Hz, J2=2.6 Hz, 1H), 7.56-7.47 (m, 2H), 6.70 (d, J=9.5 Hz, 1H), 3.87-3.82 (m, 2H), 2.98 (q, J=7.6 Hz, 2H), 1.46-1.8 (m, 3H); APCI MS m/z 351 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09221843B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-68fb290cbee84dd9839652b2fda07e16 |
| Source note | uspto-grants-2015_12 |