Buchwald–Hartwig amination → N-[5-[[3-cyano-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-cyclopropyl-4-fluorophenyl]acetamide
4% yield, run at 145 °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 | CC(=O)Nc1cc(N)c(F)cc1C1CC1 | C₁₁H₁₃FN₂O | |
| 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 | Dimethylacetamide | C₄H₉NO | |
| Product | N-[5-[[3-cyano-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-cyclopropyl-4-fluorophenyl]acetamide | C₂₁H₂₀FN₇O₂ | 3.55% |
Conditions
- Temperature
- 145 °C
Yield
- 4% of N-[5-[[3-cyano-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-cyclopropyl-4-fluorophenyl]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 | 1,4-Dioxane | 140 °C | — | 24% |
| Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphane; Bis(dibenzylideneacetone)palladium | Cesium carbonate | Dimethylacetamide | 145 °C | — | 4% (this run) |
Procedure
Copied from the source record, unedited
In a microwave tube, was Cs2CO3 (0.522 g, 1.60 mmol), N-(5-amino-2-cyclopropyl-4-fluorophenyl)acetamide (0.167 g, 0.80 mmol), Pd2dba3 (0.037 g, 0.04 mmol),5-chloro-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (0.200 g, 0.80 mmol),di-tert- butyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.034 g, 0.08 mmol). anhydrous DMA (1.0 mL) was added. The resulting mixture was bubbled through N2. Then the tube was capped. under microwave 145C for 25min. LCMS showed product and byproduct mass, did not showed SM The mixture was filtered through celite. The resulting black solution was concentrated to dryness by rotavapor. The crude product was purified by ISCO (40g, Hex to EtOAc:HEx=1;2 to 1;1 to EtOAcO) to give product (offwhite solid). HPLC showed some impurity. This offwhite so
The source
This record comes from experimental reaction archive (ord-bfef1bef76ff43f7a429af888b0d1628). Open the source and check it against what is on this page.
experimental reaction archive record ord-bfef1bef76ff43f7a429af888b0d1628 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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