Buchwald–Hartwig amination: N-(5-amino-2-cyclopropylphenyl)acetamide → N-[5-[[3-cyano-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-cyclopropylphenyl]acetamide
0% yield, run at 90 °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 | N#Cc1cnn2c(NC3COC3)cc(Cl)nc12 | C₁₀H₈ClN₅O | |
| Reactant | N-(5-amino-2-cyclopropylphenyl)acetamide | C₁₁H₁₄N₂O | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphane | C₂₉H₄₅P | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Dimethylformamide | C₃H₇NO | |
| Product | N-[5-[[3-cyano-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-cyclopropylphenyl]acetamide | C₂₁H₂₁N₇O₂ | 0% |
Conditions
- Temperature
- 90 °C
Yield
- 0% of N-[5-[[3-cyano-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-cyclopropylphenyl]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 |
|---|---|---|---|---|---|
| Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphane; Bis(dibenzylideneacetone)palladium | Cesium carbonate | Dimethylacetamide | 150 °C | — | 7% |
| Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphane; Bis(dibenzylideneacetone)palladium | Cesium carbonate | Dimethylformamide | 90 °C | — | 0% (this run) |
Procedure
Copied from the source record, unedited
Ref: _Angew. Chem. Int. Ed._ **2006** , _45_ , 6523-6527 1\. To a microwave tube was added N-(5-amino-2-cyclopropylphenyl)acetamide (0.038 g, 0.20 mmol), 5-chloro-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (0.060 g, 0.24 mmol), Cs2CO3 (0.196 g, 0.60 mmol), Pd2dba3 (0.018 g, 0.02 mmol), and di-tert-butyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.017 g, 0.04 mmol). The mixture was dissolved in DMF (0.5 mL) and sealed. The tube was de- gassed and inflated with N2. 2\. The reaction was heated at 90°C in oil-bath overnight. LCMS showed SM and byproducts and small amount of product mass. did not workup
The source
This record comes from experimental reaction archive (ord-6ca5406ed1914cc08b2221358d36ecf3). Open the source and check it against what is on this page.
experimental reaction archive record ord-6ca5406ed1914cc08b2221358d36ecf3 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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