HuagongsheHuagongshe Chemistry Print Report · For research reference only
Aniline → HCID 66955518, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Aniline | HCID 6115 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | Methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate | HCID 86665647 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 66955518 | HCID 66955518 | 49.6% |
Reaction Steps
Methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate (100 mg; 0.300 mmol), aniline (0.033 mL; 0.361 mmol), palladium acetate (2 mg, 0.009 mmol) and xantphos (10 mg; 0.018 mmol) were placed in a 2 mL reaction tube and dissolved in dioxane (1 mL), the tube was purged with argon, sealed and irradiated in a microwave oven at 160° C. for 15 min. The reaction mixture was partitioned between a saturated sodium chloride solution and dichloromethane, filtered over a phase separator filter (1PS) and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (5-40%) in heptane to yield 58 mg (39%) of the title compound as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08906906B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-93824eed90ec456fbc8726b622305bd5 |
| Source note | uspto-grants-2014_12 |