Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1,1-Trifluoro-2-iodoethane | HCID 67709 | — |
| Reactant | thieno(2,3-d)pyrimidin-4(3H)-one | HCID 2808547 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 89810746 | HCID 89810746 | 70.3% |
Reaction Steps
A mixture of thieno[2,3-d]pyrimidin-4(3H)-one (25 g, 164 mmol), 1,1,1-trifluoro-2-iodoethane (32.4 ml, 329 mmol) and cesium carbonate (53.5 g, 164 mmol) in DMF (100 ml) was heated at 100° C. for 18 h in a round bottom flask. 1 L of water was added to the reaction mixture and was extracted with ethyl acetate (3×300 ml). The combined organic phase was washed with water (500 ml), followed by brine. The organic phase was dried over MgSO4, filtrated, then concentrated in vacuo. The residue was purified by flash chromatography (0-100% ethyl acetate/DCM) to obtain the title compound (27 g, 70%). LCMS RT=0.88 min, M+H+=235.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09156853B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-74c4e24b5ab645af913210dd815cc176 |
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| Source note | uspto-grants-2015_10 |
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