Buchwald–Hartwig amination, record ord-a0aa244ac0f34a23886d9e4b9c227fa6
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 | Cn1cnc(Nc2cc(Cl)nc3c(C#N)cnn23)c1 | C₁₁H₈ClN₇ | |
| Reactant | 2-Acetylamino-4-aminotoluene | C₉H₁₂N₂O | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | C₃₃H₄₉P | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Dimethylacetamide | C₄H₉NO | |
| Product | N-[5-({3-Cyano-7-[(1-Methyl-1h-Imidazol-4-Yl)amino]pyrazolo[1,5-A]pyrimidin-5-Yl}amino)-2-Methylphenyl]acetamide | C₂₀H₁₉N₉O | 12.78% |
Conditions
- Temperature
- 100 °C
Yield
- 13% of N-[5-({3-Cyano-7-[(1-Methyl-1h-Imidazol-4-Yl)amino]pyrazolo[1,5-A]pyrimidin-5-Yl}amino)-2-Methylphenyl]acetamide.
Procedure
Copied from the source record, unedited
To a microwave vial containing N-(5-amino-2-methylphenyl)acetamide (0.096 g, 0.58 mmol), 5-chloro-7-(1-methyl-1H-imidazol-4-ylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (0.08 g, 0.29 mmol), sodium tert-butoxide (0.093 g, 0.96 mmol) and 2-Dicyclohexylphosphino-2',4',6'-tri-iso-propyl-1,1'-biphenyl (0.014 g, 0.03 mmol) was added DMA (1.8 ml). Vial was flushed with argon and to it was added Pd2(dba)3 (0.013 g, 0.01 mmol) and the reaction was heated in a MW reactor at 100 C for 50 min . Reaction was filtered through celite and the filterate diluted with EtOAC (5 ml) and the organic solution was washed with minimum amt of brine( 1X 5 ml) and organic layer dried over Na2SO4 filtered and concentrated to give crude liquid. this was purified by flash column using 5-8% MeOH: DCM (1% NH4OH) as gr
The source
This record comes from experimental reaction archive (ord-a0aa244ac0f34a23886d9e4b9c227fa6). Open the source and check it against what is on this page.
experimental reaction archive record ord-a0aa244ac0f34a23886d9e4b9c227fa6 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.