Buchwald–Hartwig amination: 2-Bromo-4-nitroanisole → 5-chloro-N-(2-methoxy-5-nitrophenyl)-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-amine
4% yield, run at 150 °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-Bromo-4-nitroanisole | C₇H₆BrNO₃ | |
| Reactant | 5-Chloro-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-amine | C₁₁H₈ClN₅ | |
| 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 | 5-chloro-N-(2-methoxy-5-nitrophenyl)-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-amine | C₁₈H₁₃ClN₆O₃ | 4% |
Conditions
- Temperature
- 150 °C
Yield
- 4% of 5-chloro-N-(2-methoxy-5-nitrophenyl)-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-amine.
Procedure
Copied from the source record, unedited
_Crude SM used_ 2-bromo-1-methoxy-4-nitrobenzene (0.029 g, 0.13 mmol), 5-chloro-4-(pyrazolo[1,5-a]pyridin-3-yl)pyrimidin-2-amine (0.031 g, 0.125 mmol) and cesium carbonate (0.057 g, 0.18 mmol) were suspended in dry dioxane (2 mL) the mixture degassed with nitrogen for 10 minutes. TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.034 g, 0.04 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.029 g, 0.05 mmol) were added and the mixture was sealed into a microwave tube. The reaction was heated to 150 °C for 2 hours in the microwave reactor and cooled to RT. Possibly product - not very much. The reaction was heated to 150 °C for 10 hours in the microwave reactor and cooled to RT. Product now c4%, both starting materials still present. Not continued.
The source
This record comes from experimental reaction archive (ord-d45c4d4f76fd453681edb48cc851d97a). Open the source and check it against what is on this page.
experimental reaction archive record ord-d45c4d4f76fd453681edb48cc851d97a 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
This is one experiment, not a rule. It says that on one occasion these species were combined under these conditions and this came out. It does not say the reaction will give the same result on your substrate, and nothing on the page has been generalised into a claim that it would.
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