Buchwald–Hartwig amination, record ord-a20b5a194b7e441a86818aba8bf8e5b1
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-(propan-2-yl)phenyl]acetamide | C₁₁H₁₆N₂O | |
| 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-propan-2-ylphenyl]acetamide | C₂₁H₂₃N₇O | 10.29% |
Conditions
- Temperature
- 140 °C
Yield
- 10% of N-[5-[[3-cyano-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-propan-2-ylphenyl]acetamide.
Procedure
Copied from the source record, unedited
In a 5 mL microwave reactor vial was charged with 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (0.070 g, 0.30 mmol), N-(5-amino-2-isopropylphenyl)acetamide (0.058 g, 0.30 mmol), Pd2(dba)3 (0.014 g, 0.01 mmol), Pd2(dba)3 (0.014 g, 0.01 mmol) and cesium carbonate (0.293 g, 0.90 mmol), the vessel was sealed with a microwave cap, and degassed and refilled with argon for 3 times. DMA (0.5 mL)was added via syringe. The resulting suspension heated at 140°C for 30mins in microwave. LCMS analysis showed product mass and byproduct. The reaction mixture was concentrated. 10% MeOH in DCM was added to the resulting residue to generate a brown suspension. This brown suspension was filtered to remove inorganic impurity. The filtrate was concentrated to give a brown crude product
The source
This record comes from experimental reaction archive (ord-a20b5a194b7e441a86818aba8bf8e5b1). Open the source and check it against what is on this page.
experimental reaction archive record ord-a20b5a194b7e441a86818aba8bf8e5b1 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.