Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Ethyl 5-chlorothiophene-2-carboxylate | HCID 521808 | — |
| Reactant | Lithium Hexamethyldisilazide | HCID 2733832 | — |
| Reactant | 2-Chloro-4-methylpyrimidine | HCID 11629607 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86657915 | HCID 86657915 | 84% |
Reaction Steps
To a solution of 2-chloro-4-methylpyrimidine (1 eq, 46.7 mmol) and ethyl 5-chlorothiophene-2-carboxylate (1.1 eq, 51.3 mmol) in anhydrous THF (50 mL) at 0° C., under N2 was added dropwise a solution of lithium bis(trimethylsilyl)amide (1 molar solution in hexanes, 2 eq, 93.3 mmol). The mixture was stirred 2 h at 5° C. Water was then added followed by 300 mL of dichloromethane. The organic layer was separated and the yellow precipitate was then filtered and dried to afford 10.7 g (84% yield) of 2-(2-chloropyrimidin-4-yl)-1-(5-chloro-2-thienyl)ethanone.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08685974B2 |
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| Source dataset | uspto-grants-2014_04 |
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| ORD ID | ord-1df0aefb2c9c4aed984d068dfe751e8f |
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| Source note | uspto-grants-2014_04 |
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