Buchwald–Hartwig amination: Chloropyrazine → 2-(alpha-Methylbenzylamino) pyrazine
43% yield, run at 70 °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 | Chloropyrazine | C₄H₃ClN₂ | |
| Reactant | 1-Phenethylamine | C₈H₁₁N | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | 2-(alpha-Methylbenzylamino) pyrazine | C₁₂H₁₃N₃ | 42.54% |
Conditions
- Temperature
- 70 °C
Yield
- 43% of 2-(alpha-Methylbenzylamino) pyrazine.
Other recorded runs with the same starting material
No other run in the library makes this product. These runs of the same class start from one of the same reactants, which is the nearest company this record has.
Procedure
Copied from the source record, unedited
To a solution of 1-phenylethanamine (212 mg, 1.75 mmol) and 2-chloropyrazine (200 mg, 1.75 mmol) in toluene (10 mL) while bubbling N2 was added binap (141 mg, 0.23 mmol), sodium tert-butoxide (235 mg, 2.44 mmol) and palladium(II) acetate (51.0 mg, 0.23 mmol). The reaction mixure was heated at 70 oC for 3 hours. The reaction was concentrated, partitioned between ethyl acetate and water. The aqueous phase was extracted 3 times with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. The crude material was loaded on a 40g silica gel column and purified on a Teledyne Isco instrument, eluting with 20% to 70% ethyl acetate in heptane to provide N-(1-phenylethyl)pyrazin-2-amine (148 mg, 42.5 %) as a solid.
The source
This record comes from experimental reaction archive (ord-74ae5f362208460ebf2f7ad1b936b06b). Open the source and check it against what is on this page.
experimental reaction archive record ord-74ae5f362208460ebf2f7ad1b936b06b 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.
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Where to next
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