Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 4-Chloro-2-methylthiopyrimidine | HCID 97113 | — |
| Reactant | Potassium Fluoride | HCID 522689 | — |
| Reactant | Stannane, tributyl(1-ethoxyethenyl)- | HCID 619414 | — |
| Catalyst | HCID 178419050 | HCID 178419050 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 23020381 | HCID 23020381 | 94.3% |
Reaction Steps
A mixture comprising 16.4 g of 4-chloro-2-methylsulfanylpyrimidine, 38 g of tributyl(1-ethoxyvinyl) tin, 1.43 g of bis(triphenylphosphine)palladium (II) dichloride and 100 ml of DMF was stirred at 80° C. for 3 hours. After cooling the reaction mixture, 300 ml of ethyl acetate and 17.8 g of potassium fluoride were added to the mixture, and the resulting mixture was stirred at room temperature overnight. After filtration with Celite, the filtrate was washed, dried and concentrated. The residue was purified by silica gel column chromatography (hexane:ethylacetate=20:1) to give 18.9 g of 4-(1-ethoxy-vinyl)-2-methylsulfanylpyrimidine.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07846933B2 |
|---|
| Source dataset | uspto-grants-2010_12 |
|---|
| ORD ID | ord-4412fbb302504dd79355a2e4bfb12edb |
|---|
| Source note | uspto-grants-2010_12 |
|---|