Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Methyl Acrylate | HCID 7294 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 4,6-Dichloro-2-methylpyrimidine | HCID 234997 | — |
| Catalyst | Tetrabutylammonium Chloride | HCID 70681 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 131733907 | HCID 131733907 | 37.5% |
Reaction Steps
To a solution of 4,6-dichloro-2-methylpyrimidine (2.45 g) and methyl acrylate (3.87 g) in DMF (20 mL) were added tris(dibenzylideneacetone)dipalladium (680 mg), N-ethyldiisopropylamine (3.90 g) and tetrabutylammonium chloride (82 mg) under a nitrogen atmosphere, and the mixture was stirred at 90° C. for 15 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.20 g) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09181186B2 |
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| Source dataset | uspto-grants-2015_11 |
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| ORD ID | ord-0d9d64640e004261b10fe114c4beb93e |
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| Source note | uspto-grants-2015_11 |
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