HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 538458Generated: October 27, 2026
1,2-Dimethoxyethane → Methyl 2-(6-chloropyrimidin-4-yl)benzoate
https://huagongshe.com/reaction/538458
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1,2-Dimethoxyethane | HCID 8071 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2,4-Dichloropyrimidine | HCID 77531 | — |
| Reactant | Methyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate | HCID 2760076 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Product | Methyl 2-(6-chloropyrimidin-4-yl)benzoate | HCID 24902049 | 31.6% |
Reaction Steps
A mixture of methyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (2.0 g), 2,6-dichloropyrimidine (1.4 g), sodium carbonate (2.4 g), tetrakis(triphenylphosphine)palladium(0) (0.44 g), water (2.0 mL) and DME (10 mL) was stirred at 150° C. for 1 hr under microwave irradiation. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.60 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08865717B2 |
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| Source dataset | uspto-grants-2014_10 |
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| ORD ID | ord-9af26bda510a4f39880ab7c7e3048246 |
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| Source note | uspto-grants-2014_10 |
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