Buchwald–Hartwig amination, record ord-9f0febad39ec4abd95b00a68a93da5f3
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 | 4-chloro-N-[(1S)-1-(5-fluoropyrimidin-2-yl)ethyl]-6-morpholin-4-yl-1,3,5-triazin-2-amine | C₁₃H₁₅ClFN₇O | |
| Reactant | 2-Amino-5-methylthiazole | C₄H₆N₂S | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | N-[(1S)-1-(5-Fluoropyrimidin-2-yl)ethyl]-N'-(5-methyl-1,3-thiazol-2-yl)-6-morpholin-4-yl-1,3,5-triazine-2,4-diamine | C₁₇H₂₀FN₉OS | 20.67% |
Conditions
- Temperature
- 95 °C
Yield
- 21% of N-[(1S)-1-(5-Fluoropyrimidin-2-yl)ethyl]-N'-(5-methyl-1,3-thiazol-2-yl)-6-morpholin-4-yl-1,3,5-triazine-2,4-diamine.
Procedure
Copied from the source record, unedited
(S)-4-chloro-N-(1-(5-fluoropyrimidin-2-yl)ethyl)-6-morpholino-1,3,5-triazin-2-amine (100 mg, 0.29 mmol), 5-methylthiazol-2-amine (50.4 mg, 0.44 mmol), BINAP (18.33 mg, 0.03 mmol), Pd2(dba)3 (13.48 mg, 0.01 mmol) and Cs2CO3 (240 mg, 0.74 mmol) were combined in a microwave reaction tube and vacuum purged. The tube was then charged with nitrogen and dioxane (0.589 mL) was added. The tube was then evacuated again and placed under a nitrogen balloon for 8 hours. LC/MS confirmed formation of the product (m+1 = 418) at t= 2.07 min. The reaction mixture was concentrated in vacuo leaing a brown solid (472 mg). This material was the redissolved in EtOAc, filtered through Celite, washed with water and dried with Na2SO4. Concentration in vacuo gave a rust solid (272 mg). This material was purified by
The source
This record comes from experimental reaction archive (ord-9f0febad39ec4abd95b00a68a93da5f3). Open the source and check it against what is on this page.
experimental reaction archive record ord-9f0febad39ec4abd95b00a68a93da5f3 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.