Buchwald–Hartwig amination, record ord-a242bdcea6fd4820b97f40b83c063cc9
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 | N#Cc1cnn2c(NC3COC3)cc(Cl)nc12 | C₁₀H₈ClN₅O | |
| Reactant | N-(5-amino-2-cyclopropylphenyl)acetamide | C₁₁H₁₄N₂O | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphane | C₂₉H₄₅P | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Dimethylacetamide | C₄H₉NO | |
| Product | N-[5-[[3-cyano-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-cyclopropylphenyl]acetamide | C₂₁H₂₁N₇O₂ | 6.96% |
Conditions
- Temperature
- 150 °C
Yield
- 7% of N-[5-[[3-cyano-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-cyclopropylphenyl]acetamide.
Procedure
Copied from the source record, unedited
A 10 mL microwave reactor vial was charged with 5-chloro-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (80 mg, 0.32 mmol), N-(5-amino-2-cyclopropylphenyl)acetamide (67.1 mg, 0.35 mmol), Cs2CO3 (313 mg, 0.96 mmol), Pd2(dba)3 (14.67 mg, 0.02 mmol) and 2-Di-t- butylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl (13.61 mg, 0.03 mmol). The suspended in DMA (.5 mL), added via syringe. The resulting brown suspension was stirred under nitrogen, then microwave vial capped and heated at 150 °C under microwave irradiation for 20 min. LCMS indicated formation of product. The cooled reaction mixture was put through vacuum filtration and concentrated in rotovap. The crude material was purified by ISCO using MeOH and EtOAc (1:10). The solid was suspended in water, stirred for 12 h at rt,
The source
This record comes from experimental reaction archive (ord-a242bdcea6fd4820b97f40b83c063cc9). Open the source and check it against what is on this page.
experimental reaction archive record ord-a242bdcea6fd4820b97f40b83c063cc9 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.