HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 4-Benzyl-2-chloro-6-methyl-pyrimidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 4-Benzyl-2,6-dichloropyrimidine | HCID 46223071 | — |
| Reactant | HCID 178477796 | HCID 178477796 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-Benzyl-2-chloro-6-methyl-pyrimidine | HCID 86633618 | 83% |
Reaction Steps
4-Benzyl-2,6-dichloro-pyrimidine (2.5 g, 10.5 mmol) was dissolved in tetrahydrofuran (40 mL) under an atmosphere of nitrogen and subsequently treated with dimethylzinc (2M in toluene, 5.76 mL) and tetrakis(triphenylphosphine)palladium(0) (245 mg). After stirring for 18 h at ambient temperature, ethyl acetate and water were added, the phases separated and the aqueous layer was extracted twice with ethyl acetate. The combined organic phases were dried over magnesium sulfate and evaporated under reduced pressure. Column chromatography on silica gel using heptane/ethyl acetate 9:1 v/v) as eluent afforded the title compound (1.89 g, 83%) as colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08962834B2 |
| Source dataset | uspto-grants-2015_02 |
| ORD ID | ord-cc65dc63b2f9491db13e63ec212cf74f |
| Source note | uspto-grants-2015_02 |