Buchwald–Hartwig amination, record ord-971b196dec9043e8982df95c855b9cba
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 | Benzene, 1-iodo-3-(trifluoromethyl)- | C₇H₄F₃I | |
| Reactant | 2-Amino-5-bromo-4-methoxypyrimidine | C₅H₆BrN₃O | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | 5-bromo-4-methoxy-N-[3-(trifluoromethyl)phenyl]pyrimidin-2-amine | C₁₂H₉BrF₃N₃O | 8.77% |
Conditions
- Temperature
- 80 °C
Yield
- 9% of 5-bromo-4-methoxy-N-[3-(trifluoromethyl)phenyl]pyrimidin-2-amine.
Procedure
Copied from the source record, unedited
_EN06995-11\Reaction_ and many others **_Aim:-_ prepare target for further use.** 1-iodo-3-(trifluoromethyl)benzene (0.215 ml, 1.49 mmol), 5-bromo-4-methoxypyrimidin-2-amine (0.254 g, 1.24 mmol), PALLADIUM(II) ACETATE (0.014 g, 0.06 mmol), rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthalene (0.054 g, 0.09 mmol) and cesium carbonate (0.487 g, 1.49 mmol) were mixed in toluene (5ml), purged with nitrogen and stirred in a sealed tube at 80 °C overnight. LCMS: pH = 3, 2 minute run time, Rt = 0.66 min (32% by UV), m/z: 204 (MH+) \- 316 (M-H-) - ?; Rt = 1.10 min (15% by UV), m/z: 257, 306 (MH+) - 316 (M-H-) - ?; Rt = 1.28 min (25% by UV), m/z: 350, (MH+) product ?. The reaction mixture was diluted with EtOAc (20 ml), filtered through a celite pad and concentrated to give 902 mg yellow oil. TL
The source
This record comes from experimental reaction archive (ord-971b196dec9043e8982df95c855b9cba). Open the source and check it against what is on this page.
experimental reaction archive record ord-971b196dec9043e8982df95c855b9cba 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.