Potassium Fluoride → HCID 117821238, compound
Reaction equation
C([Sn](CCCC)(CCCC)[C:6]([O:8][CH2:9][CH3:10])=[CH2:7])CCC.[Cl:19][C:20]1[N:25]=[C:24](Cl)[CH:23]=[C:22]([CH:27]([O:29][CH2:30][C:31]([F:34])([F:33])[F:32])[CH3:28])[N:21]=1.[F-].[K+]>CN(C)C=O.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:19][C:20]1[N:25]=[C:24]([C:6]([O:8][CH2:9][CH3:10])=[CH2:7])[CH:23]=[C:22]([CH:27]([O:29][CH2:30][C:31]([F:34])([F:33])[F:32])[CH3:28])[N:21]=1Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
Tributyl(1-ethoxyvinyl)stannane (0.466 mL, 1.38 mmol) was added to a degased solution of 2,4-dichloro-6-(1-(2,2,2-trifluoroethoxy)ethyl)pyrimidine (0.379 g, 1.38 mmol) and bis(triphenylphosphine)palladium chloride (0.019 g, 0.03 mmol) in dimethylformamide (8 mL) under nitrogen. The mixture was heated at 80° C. for 1.5 h, then cooled and poured into solution of potassium fluoride (2 g) in water (40 mL). The mixture was extracted with MTBE (2×50 mL), the organic phase was washed with water (30 mL), dried over sodium sulfate and concentrated in vacuum. The residue was purified by column chromatography on silica eluting with dichloromethane to yield the title product, 350 mg (82%).
Workup
- temperaturecooled
- extractionThe mixture was extracted with MTBE (2×50 mL)
- washthe organic phase was washed with water (30 mL)
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuum
- customThe residue was purified by column chromatography on silica eluting with dichloromethane
Sources & evidence
- ORD record
- ord-e226328bee2a4509a2ce6cfb6bf2c50e
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09439904B2
Reaction notes
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