Buchwald–Hartwig amination, record ord-6baac44dbbb745bfaa3ee3e69cefbcee
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 | Cc1cc(Cl)ncc1-c1ccc(-c2nc3c(CO)cccc3c(=O)[nH]2)cc1 | C₂₁H₁₆ClN₃O₂ | |
| Reactant | (S)-1,2-Dimethylpiperazine | C₆H₁₄N₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl | C₃₀H₄₃O₂P | |
| Catalyst | (RuPhos) palladium(II) phenethylamine chloride (1:1 MTBE solvate) | C₄₃H₆₅ClNO₃PPd | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | 2-[4-[6-[(3S)-3,4-dimethylpiperazin-1-yl]-4-methyl-3-pyridinyl]phenyl]-8-(hydroxymethyl)-1H-quinazolin-4-one | C₂₇H₂₉N₅O₂ | 26.54% |
Conditions
- Temperature
- 110 °C
Yield
- 27% of 2-[4-[6-[(3S)-3,4-dimethylpiperazin-1-yl]-4-methyl-3-pyridinyl]phenyl]-8-(hydroxymethyl)-1H-quinazolin-4-one.
Procedure
Copied from the source record, unedited
A mixture of CHLORO(2-DICYCLOHEXYLPHOSPHINO-2',6'-DI-I- PROPOXY-1,1'-BIPHENYL)[2-(2-AMINOETHYLPHENYL)]PALLADIUM(II), METHYL-T- BUTYLETHER ADDUCT (Ru Phos Pd cycle) (43.2 mgs, 0.1eq), sodium tert-butoxide (229 mg, 2.38 mmol), 2-(4-(6-chloro-4-methylpyridin-3-yl)phenyl)-8-(hydroxymethyl)quinazolin-4(3H)-one (250 mg, 0.53 mmol) , (S)-1,2-dimethylpiperazine (198 mg, 1.06 mmol) in dioxane (25ml) was stirred at 105°C for 1hr, LCMS only detected a small peak as product. 2 more equivalent of sodium tert-butoxide was added to the mixture and stirred for overnight under N2, LCMS indicated major peak as starting material; another batch of Ru phos pd cycle was added to the mixture, and the mixture was stirred at 120°C for 1.5hrs. LCMS indicated the completion of reaction. The solvent was removed by co
The source
This record comes from experimental reaction archive (ord-6baac44dbbb745bfaa3ee3e69cefbcee). Open the source and check it against what is on this page.
experimental reaction archive record ord-6baac44dbbb745bfaa3ee3e69cefbcee 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.