Buchwald–Hartwig amination, record ord-bcc19de9bb794d1ea8d67a62b78fce0d
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 | Cn1ccc(Nc2cc(Cl)nc3c(C#N)cnn23)n1 | C₁₁H₈ClN₇ | |
| Reactant | 2-Acetylamino-4-aminotoluene | C₉H₁₂N₂O | |
| 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-[(1-methylpyrazol-3-yl)amino]pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-methylphenyl]acetamide | C₂₀H₁₉N₉O | 33.24% |
Conditions
- Temperature
- 150 °C
Yield
- 33% of N-[5-[[3-cyano-7-[(1-methylpyrazol-3-yl)amino]pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-methylphenyl]acetamide.
Procedure
Copied from the source record, unedited
in microwave tube was 5-chloro-7-(1-methyl-1H-pyrazol-3-ylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (80 mg, 0.29 mmol), N-(5-amino-2-methylphenyl)acetamide (48.0 mg, 0.29 mmol), and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (16.91 mg, 0.03 mmol) in DMA (0.5 mL).Pd2(dba)3 (13.38 mg, 0.01 mmol) and cesium carbonate (105 mg, 0.32 mmol) were added. degassed, filled with N2.capped. then microwave 150C for 30 min. added 2 mL of MeOH, filtered through celite. concentrated. The residue was purified by ISCO (Hex to Hex:EtOAc=1:4 to 1:1 to EtOAc), collected prod fractions. concentrated to give offwhite solid. This solid was washed with 0.5 mL of EtOAc to give pure prod
The source
This record comes from experimental reaction archive (ord-bcc19de9bb794d1ea8d67a62b78fce0d). Open the source and check it against what is on this page.
experimental reaction archive record ord-bcc19de9bb794d1ea8d67a62b78fce0d 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.