Buchwald–Hartwig amination, record ord-7d21d2aa9b9646bf85b8f593faa79359
One recorded run of this reaction. Below is what the source recorded, and nothing added to it.
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 | 1,4-Dioxane | C₄H₈O₂ | |
| Product | N-[5-[[3-cyano-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-cyclopropyl-4-fluorophenyl]acetamide | C₂₁H₂₀FN₇O₂ | 23.91% |
Conditions
- Temperature
- 140 °C
Yield
- 24% of N-[5-[[3-cyano-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-cyclopropyl-4-fluorophenyl]acetamide.
Procedure
Copied from the source record, unedited
dioxane (4 mL) was adde to the mixture of N-(5-amino-2-cyclopropyl-4-fluorophenyl)acetamide (100 mg, 0.48 mmol), 5-chloro-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (132 mg, 0.53 mmol),cesium carbonate (469 mg, 1.44 mmol), Pd2(dba)3 (44.0 mg, 0.05 mmol), di-tert-butyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (40.8 mg, 0.10 mmol) in 5 ml microwave vial. N2 flow was bubbled through for 3 mins. Then the reaction solution was sealed with cap, degassed and refilled with argon 3 times. The resulting solution was heated at 140°C for 40 mins in microwave. LC/MS showed desired product as major peak. After the crude solution was concentrated, the crude residue was purified by chromatography (100% EtOAc to 3% MeOH in EtOAc). N-(5-(3-cyano-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrim
The source
This record comes from experimental reaction archive (ord-7d21d2aa9b9646bf85b8f593faa79359). Open the source and check it against what is on this page.
experimental reaction archive record ord-7d21d2aa9b9646bf85b8f593faa79359 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.