HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dichloromethane → (E)-methyl 5-(2-ethoxyvinyl)-2-(methylthio)pyrimidine-4-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Methyl 5-bromo-2-(methylsulfanyl)pyrimidine-4-carboxylate | HCID 2794729 | — |
| Reactant | 1-Ethoxyethene-2-boronic acid pinacol ester | HCID 21973908 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (E)-methyl 5-(2-ethoxyvinyl)-2-(methylthio)pyrimidine-4-carboxylate | HCID 89996170 | 63% |
Reaction Steps
A solution of (E)-2-(2-ethoxyvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Preparation 29, 4.34 g, 21.91 mmol), methyl 5-bromo-2-(methylthio)pyrimidine-4-carboxylate (Preparation 30, 3.81 g, 14.48 mmol) and Pd(dppf)Cl2.DCM (505 mg, 0.618 mmol) was dissolved in THF (45 mL) and 2M sodium carbonate in water (15 mL) and heated to 65° C. for 18 hours. The mixture was diluted with EtOAc and quenched with brine. The aqueous layer was extracted with EtOAc three times. The combined organic layers were washed with water and brine, dried and concentrated. The residue was purified by silica gel column chromatography eluting with 0 to 10% EtOAc in cyclohexane to give the title compound (2.30 g, 63%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09409907B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-7430976adfc344cebaf6eb66eb6ba3a0 |
| Source note | uspto-grants-2016_08 |