Buchwald–Hartwig amination, record ord-6a2cb6eee4e6411fbe36a812955f2574
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 | CC(=O)Nc1cc(N)ccc1N1CCC[C@@H](N(C)C)C1 | C₁₅H₂₄N₄O | |
| 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 | N-[5-[[3-cyano-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-[(3R)-3-(dimethylamino)piperidin-1-yl]phenyl]acetamide | C₂₅H₃₁N₉O | 7.29% |
Conditions
- Temperature
- 150 °C
Yield
- 7% of N-[5-[[3-cyano-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-[(3R)-3-(dimethylamino)piperidin-1-yl]phenyl]acetamide.
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 (120mg, 0.51 mmol), (R)-N-(5-amino-2-(3-(dimethylamino)piperidin-1-yl)phenyl)acetamide (142 mg, 0.51 mmol), and cesium carbonate (335 mg, 1.03 mmol) in DMA (0.5 mL) (),Pd2(dba)3 (23.51 mg, 0.03 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (29.7 mg, 0.05 mmol) were added. to give a brown suspension. The vial was filled with N2, 150C microwave for 30 min. LCMS showed completion. added MeOH (2 mL), filtered. The solvent was removed by ratovapor to yield stick oil. The crude product was loaded on ISCO (Hex to Hex:EtOAc To EtOAc to EtOAc:MeOH:Et3N=10:1:0.1) to give sticky oil. The product was not pure. It was purifed by to give (R)-N-(5-(3-cyano-7-(cyclopropylamino)pyrazolo
The source
This record comes from experimental reaction archive (ord-6a2cb6eee4e6411fbe36a812955f2574). Open the source and check it against what is on this page.
experimental reaction archive record ord-6a2cb6eee4e6411fbe36a812955f2574 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.