Buchwald–Hartwig amination, record ord-01bb5c09bf964bc095ad839c85efa1ae
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 | 29.37% |
Conditions
- Temperature
- 150 °C
Yield
- 29% 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 (80 mg, 0.34 mmol), [Reactants], and cesium carbonate (145 mg, 0.45 mmol) in DMA (0.5 mL) ([VOLUME]),Pd2(dba)3 (15.68 mg, 0.02 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (19.81 mg, 0.03 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 solid. This yellow solid was washed with EtOAc(1mL) and Et2O(2mL) to give 50 mg pure compound. NMR, 1H,HPLC are OK, see attachment
The source
This record comes from experimental reaction archive (ord-01bb5c09bf964bc095ad839c85efa1ae). Open the source and check it against what is on this page.
experimental reaction archive record ord-01bb5c09bf964bc095ad839c85efa1ae 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.