HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-(4-Chlorophenoxy)-1-(4-(6-(4-fluorophenyl)-2-methylthieno[2,3-d]pyrimidin-4-yl)piperazin-1-yl)ethanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Reactant | 2-(4-Chlorophenoxy)-1-(piperazin-1-yl)ethanone | HCID 1074760 | — |
| Reactant | HCID 66758458 | HCID 66758458 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 2-(4-Chlorophenoxy)-1-(4-(6-(4-fluorophenyl)-2-methylthieno[2,3-d]pyrimidin-4-yl)piperazin-1-yl)ethanone | HCID 56941893 | 88.5% |
Reaction Steps
To a solution of 6-(4-fluorophenyl)-2-methylthieno[2,3-d]pyrimidin-4(3H)-one (40 mg, 0.15 mmol) and BOP (88 mg, 0.20 mmol) in CH3CN (1 ml) was added DBU (34 μl, 0.23 mmol). After stirring for 10 minutes at room temperature, 2-(4-chlorophenoxy)-1-(piperazin-1-yl)ethanone (59 mg, 0.23 mmol) was added. The reaction was stirred at room temperature overnight and then heated at 60° C. for 4 hours. The solvents were removed under reduced pressure, and the crude residue was purified by flash chromatography on silica gel (CH2Cl2/MeOH 100:1) to yield the title compound as a white solid (66 mg, 86%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09193741B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-8fb0cab007944470995fe20245e311a7 |
| Source note | uspto-grants-2015_11 |