Water → HCID 89810746, compound
Reaction equation
[N:1]1[C:6]2[S:7][CH:8]=[CH:9][C:5]=2[C:4](=[O:10])[NH:3][CH:2]=1.[F:11][C:12]([F:16])([F:15])[CH2:13]I.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[F:11][C:12]([F:16])([F:15])[CH2:13][N:3]1[C:4](=[O:10])[C:5]2[CH:9]=[CH:8][S:7][C:6]=2[N:1]=[CH:2]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
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.
Workup
- extractionwas extracted with ethyl acetate (3×300 ml)
- washThe combined organic phase was washed with water (500 ml)
- dry with materialThe organic phase was dried over MgSO4
- filtrationfiltrated
- concentrationconcentrated in vacuo
- customThe residue was purified by flash chromatography (0-100% ethyl acetate/DCM)
Sources & evidence
- ORD record
- ord-74c4e24b5ab645af913210dd815cc176
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156853B2
Reaction notes
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