Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Chloropyrimidine | HCID 74404 | — |
| Reactant | HCID 178490772 | HCID 178490772 | — |
| Catalyst | Copper | HCID 23978 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 66888334 | HCID 66888334 | 18.2% |
Reaction Steps
According to Scheme 2, Step 5: A mixture of 4-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl)thiazol-2-ol (0.99 mmol, 300 mg), 2-chloropyrimidine (0.99 mmol, 114 mg), copper (0.20 mmol, 12.6 mg) and cesium carbonate (2.99 mmol, 973 mg) in DMF (3.3 mL) was stirred at 160° C. under microwave conditions for 45 minutes. Then, the reaction mixture was diluted with EtOAc and was washed with water. The organic phase was dried over MgSO4, was filtered and was evaporated. The crude mixture was purified by flash chromatography over silica gel using cyclohexane/EtOAc (80:20 to 60:40) as eluent to yield 4-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl)-2-(pyrimidin-2-yloxy)thiazole (0.18 mmol, 67 mg, 18%) as a yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08513252B2 |
|---|
| Source dataset | uspto-grants-2013_08 |
|---|
| ORD ID | ord-060d80d204b7470eafe8a8b83064d141 |
|---|
| Source note | uspto-grants-2013_08 |
|---|