Buchwald–Hartwig amination: 2,4-Dichloropyridine → N-(4-chloro-2-pyridinyl)-4,5-dimethyl-1,3-oxazol-2-amine
15% yield, run at 140 °C, as recorded by experimental reaction archive. The written procedure is below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 2,4-Dichloropyridine | C₅H₃Cl₂N | |
| Reactant | 4,5-Dimethyloxazol-2-amine | C₅H₈N₂O | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | N-(4-chloro-2-pyridinyl)-4,5-dimethyl-1,3-oxazol-2-amine | C₁₀H₁₀ClN₃O | 15.2% |
Conditions
- Temperature
- 140 °C
Yield
- 15% of N-(4-chloro-2-pyridinyl)-4,5-dimethyl-1,3-oxazol-2-amine.
Procedure
Copied from the source record, unedited
Objective: Repeat of experiment in an attempt to improve isolated yield using different normal phase eluent system (isolation was problematic for ). Pd2(dba)3 (22.89 mg, 0.025 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (43.4 mg, 0.075 mmol), 2,4-dichloropyridine (148 mg, 1.00 mmol), cesium carbonate (652 mg, 2.00 mmol) and 4,5-dimethyloxazol-2-amine (112 mg, 1.00 mmol) were added to an oven dried microwave vial, the vial was capped and placed under an inert atmosphere, dioxane (4 mL) was added and the resulting mixture was heated to 140 °C for 1 h by microwave irradiation under a nitrogen atmosphere. The crude product was purified by flash silica chromatography, elution gradient 0 to 3% methanolic ammmonia (7 M) in DCM. Pure fractions were evaporated to dryness to afford P1
The source
This record comes from experimental reaction archive (ord-b88a57a3139142d0b67529e7ea94eb7c). Open the source and check it against what is on this page.
experimental reaction archive record ord-b88a57a3139142d0b67529e7ea94eb7c from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.
How to read this record
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