Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethyl Ether | HCID 8254 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Thiopheneboronic acid | HCID 2733960 | — |
| Reactant | HCID 60204554 | HCID 60204554 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 60204557 | HCID 60204557 | — |
Reaction Steps
1-(2-(4-(5-Bromothiophen-2-yl)-5-methylpyrimidin-2-ylamino)ethyl)imidazolidin-2-one (0.1 g, 0.26 mmol), thiophen-2-ylboronic acid (0.066 g, 0.52 mmol), and sodium carbonate (0.26 mL of 2 M solution, 0.52 mmol) were added to a microwave tube containing dimethyl ether (2 mL). The tube was flushed with nitrogen and tetrakis(triphenylphosphine)palladium (0.06 g, 0.054 mmol) was added. The tube was capped and heated to 145° C. for 20 min in a Personal Chemistry microwave. The reaction was diluted with a mixture of 2:1 dichloromethane and methanol (9 mL), filtered through a pad of celite, washed with saturated aqueous sodium bicarbonate, water and brine. The organic layer was dried with sodium sulfate, concentrated in vacuo and purified by flash chromatography on silica gel using a gradient 2 to 10% of methanol in dichloromethane to afford a yellow solid. Yield=0.036 g. MS (M+H)+ 386.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07858785B2 |
|---|
| Source dataset | uspto-grants-2010_12 |
|---|
| ORD ID | ord-e0e9b33342fc44d28d7c73b5c95f4ee3 |
|---|
| Source note | uspto-grants-2010_12 |
|---|