Buchwald–Hartwig amination, record ord-1a02b93898c84c3a8a0ec8185fbf85c5
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 | 5-Chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile | C₁₀H₈ClN₅ | |
| Reactant | N-[5-amino-2-[2-(dimethylamino)ethyl-methylamino]phenyl]acetamide | C₁₃H₂₂N₄O | |
| 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 | Dimethylacetamide | C₄H₉NO | |
| Product | Acetamide, N-[5-[[3-cyano-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-[[2-(dimethylamino)ethyl]methylamino]phenyl]- | C₂₃H₂₉N₉O | 22.45% |
Conditions
- Temperature
- 150 °C
Yield
- 22% of Acetamide, N-[5-[[3-cyano-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-[[2-(dimethylamino)ethyl]methylamino]phenyl]-.
Procedure
Copied from the source record, unedited
In a 40mL vial (t=g) was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (200 mg, 0.86 mmol), N-(5-amino-2-((2-(dimethylamino)ethyl)(methyl)amino)phenyl)acetamide (214 mg, 0.86 mmol), and cesium carbonate (363 mg, 1.11 mmol) in DMA (0.5 mL) ([VOLUME]),Pd2(dba)3 (39.2 mg, 0.04 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (49.5 mg, 0.09 mmol) were added. to give a brown suspension. The vial was filled with N2, 150C microwave for 30 min. LCMS showed completion. concentrated. loaded on ISCO (Hex to Hex:EtOAc To EtOAc:MeOH=10:1 to EtOAc:MeOH:Et3N=10:1:0.1) to give yellow sticky oil. tried to use EtOAc(1 mL) as solvent to make the product to form crys. finally the solid was formed and washed with EtOA (1mL) and Et2O(2mL) to give 86mg white solid N
The source
This record comes from experimental reaction archive (ord-1a02b93898c84c3a8a0ec8185fbf85c5). Open the source and check it against what is on this page.
experimental reaction archive record ord-1a02b93898c84c3a8a0ec8185fbf85c5 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.