Buchwald–Hartwig amination: 5-Chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile → N-[5-[[3-cyano-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-methylphenyl]acetamide
0% yield, run at 120 °C, as recorded by experimental reaction archive. The written procedure is below. One of 2 recorded runs making this product; all of them are compared below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 5-Chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile | C₁₀H₈ClN₅ | |
| Reactant | 2-Acetylamino-4-aminotoluene | C₉H₁₂N₂O | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 2-(Dicyclohexylphosphino)biphenyl | C₂₄H₃₁P | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Dimethylacetamide | C₄H₉NO | |
| Product | N-[5-[[3-cyano-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-methylphenyl]acetamide | C₁₉H₁₉N₇O | 0% |
Conditions
- Temperature
- 120 °C
Yield
- 0% of N-[5-[[3-cyano-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-methylphenyl]acetamide.
Every recorded run making this product
2 runs of this class made the same product and differed in what else was in the flask. They are listed from the highest yield down, with this page's run marked.
| Catalyst | Reagents | Solvent | Temp. | Time | Yield |
|---|---|---|---|---|---|
| 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine); Bis(dibenzylideneacetone)palladium | Cesium carbonate | Dimethylacetamide | 150 °C | — | 23% |
| 2-(Dicyclohexylphosphino)biphenyl; Bis(dibenzylideneacetone)palladium | sodium 2-methylpropan-2-olate | Dimethylacetamide | 120 °C | — | 0% (this run) |
Procedure
Copied from the source record, unedited
In a 25 mL round-bottomed flask (t=g) was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (40 mg, 0.17 mmol), Pd2(dba)3 (7.84 mg, 8.56 µmol), and [Reactants] in DMA (1.5 mL) ([VOLUME]) to give a black suspension.[Reactants] and N-(5-amino-2-methylphenyl)acetamide (28.1 mg, 0.17 mmol) were added. stirred at 110C for 2 days. TLC showed major is SM, small amount of product was formed/ did not workup LCMS showed 349 mass ??
The source
This record comes from experimental reaction archive (ord-9d52138831044592b5c7c5511d53f49c). Open the source and check it against what is on this page.
experimental reaction archive record ord-9d52138831044592b5c7c5511d53f49c 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.
The pathway is a separate question, kept on separate pages. A mechanism here is the canonical arrow pushing for a class, run on real structures and labelled rule-derived. It is not evidence, and this record is not a mechanism.
Where to next
More Buchwald–Hartwig amination records
Other runs of this class, one page per distinct transformation.
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