HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 6-(4,4-Dimethylcyclohexyl)-4-[(1,1-dioxidothiomorpholin-4-yl)methyl]-2-methylthieno[2,3-d]pyrimidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Thiomorpholine 1,1-dioxide | HCID 6484228 | — |
| Reactant | [6-(4,4-Dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl methanesulfonate | HCID 118023751 | — |
| Solvent | Water | HCID 962 | — |
| Product | 6-(4,4-Dimethylcyclohexyl)-4-[(1,1-dioxidothiomorpholin-4-yl)methyl]-2-methylthieno[2,3-d]pyrimidine | HCID 91754521 | 76.9% |
Reaction Steps
To a mixture of thiomorpholine-1,1-dioxide (70 mg) and DMF (4 mL) were added [6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl methanesulfonate (120 mg) and TEA (150 μL), followed by stirring at room temperature overnight. To the reaction mixture was added water, followed by extraction with EtOAc. The organic layer was washed with brine, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by basic silica gel column (hexane/EtOAc) to obtain 6-(4,4-dimethylcyclohexyl)-4-[(1,1-dioxidothiomorpholin-4-yl)methyl]-2-methylthieno[2,3-d]pyrimidine (102 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09051339B2 |
| Source dataset | uspto-grants-2015_06 |
| ORD ID | ord-84969f3147b04110b27e3a10b949f47b |
| Source note | uspto-grants-2015_06 |