Buchwald–Hartwig amination: 2-Acetylamino-4-aminotoluene → N-[5-({3-Cyano-7-[(1-Methyl-1h-Imidazol-4-Yl)amino]pyrazolo[1,5-A]pyrimidin-5-Yl}amino)-2-Methylphenyl]acetamide
29% yield, run at 100 °C, as recorded by experimental reaction archive. The written procedure is below.
The atoms, from reactants to products
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 | 29.32% |
Conditions
- Temperature
- 100 °C
Yield
- 29% 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 containingN-(5-amino-2-methylphenyl)acetamide (0.120 g, 0.73 mmol), 5-chloro-7-(1-methyl-1H-imidazol-4-ylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (0.1 g, 0.37 mmol) ,sodium 2-methylpropan-2-olate (0.116 g, 1.21 mmol) and 2-Dicyclohexylphosphino-2',4',6'-tri-iso-propyl-1,1'-biphenyl (0.017 g, 0.04 mmol)was added DMA (2.2 ml). Vial was flushed with argon and to it was added Pd2(dba)3 (0.017 g, 0.02 mmol) and the reaction was heated in a MW reactor at 100 ° C for 60 min.Reaction was filtered, and filterate concentrated under reduced pressure to give dark red gum. This was suspended in 10% MeOH : DCM (10 ml) filtered and filterate concentrated to give crude solid. This was purified by flash column using 5-8% MeoH :DCM (1% NH4OH) to give 75 mg of pale yellow solid (EN0
The source
This record comes from experimental reaction archive (ord-85b6b1948aa842f2a19dc52c1d84fd97). Open the source and check it against what is on this page.
experimental reaction archive record ord-85b6b1948aa842f2a19dc52c1d84fd97 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
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