Buchwald–Hartwig amination: 5-Bromo-2-iodo-4-methoxypyrimidine → 5-bromo-N-ethyl-4-methoxy-N-phenylpyrimidin-2-amine
54% yield, run at 60 °C, as recorded by experimental reaction archive. The written procedure is below. One of 2 recorded runs making this product; all of them are compared below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 5-Bromo-2-iodo-4-methoxypyrimidine | C₅H₄BrIN₂O | |
| Reactant | N-Ethylaniline | C₈H₁₁N | |
| Reagent | Sodium 2-methylbutan-2-olate | C₅H₁₁NaO | |
| Catalyst | Bis(adamantan-1-yl)(butyl)phosphane | C₂₄H₃₉P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | 5-bromo-N-ethyl-4-methoxy-N-phenylpyrimidin-2-amine | C₁₃H₁₄BrN₃O | 53.74% |
Conditions
- Temperature
- 60 °C
Yield
- 54% of 5-bromo-N-ethyl-4-methoxy-N-phenylpyrimidin-2-amine.
Every recorded run making this product
2 runs of this class made the same product and differed in what else was in the flask. They are listed from the highest yield down, with this page's run marked.
| Catalyst | Reagents | Solvent | Temp. | Time | Yield |
|---|---|---|---|---|---|
| 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine); Palladium (II) acetate | Sodium 2-methylbutan-2-olate | Toluene | 100 °C | — | 71% |
| Bis(adamantan-1-yl)(butyl)phosphane; Palladium (II) acetate | Sodium 2-methylbutan-2-olate | Toluene | 60 °C | — | 54% (this run) |
Procedure
Copied from the source record, unedited
5-bromo-2-iodo-4-methoxypyrimidine (0.086 g, 0.27 mmol), diacetoxypalladium (2.78 mg, 0.01 mmol), di((3S,5S,7S)-adamantan-1-yl)(butyl)phosphine (8.88 mg, 0.02 mmol) and sodium 2-methylbutan-2-olate (0.033 g, 0.30 mmol) were added to a micro vial. Then N-ethylaniline (0.031 mL, 0.25 mmol) in toluene (1.5 mL) was added to the reaction mixture. The vial was sealed and evacuated and flushed with nitrogen and then stirred at 60°C o/n. LC/MS showed product formation. The reaction mixture was cooled to rt and then filtered over celite. The crude product was diluted with 25 ml of DCM and then washed with sat. NaHCO3 followed by brine. The organic phase was dried over a phase separator and then concentrated to dryness. **No LC/MS data due to database failure over three months and was only saved lo
The source
This record comes from experimental reaction archive (ord-8bbed4d3f8cb496989e49be7e55b89ca). Open the source and check it against what is on this page.
experimental reaction archive record ord-8bbed4d3f8cb496989e49be7e55b89ca 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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