Buchwald–Hartwig amination: 3-(6-Bromo-2-pyridinyl)-1,3-oxazinan-2-one → 3-[6-[(4-Methyl-1,3-thiazol-2-yl)amino]-2-pyridinyl]-1,3-oxazinan-2-one
44% yield, run at 120 °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 | 3-(6-Bromo-2-pyridinyl)-1,3-oxazinan-2-one | C₉H₉BrN₂O₂ | |
| Reactant | 2-Amino-4-methylthiazole | C₄H₆N₂S | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium | C₃₄H₂₈O₂Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | 3-[6-[(4-Methyl-1,3-thiazol-2-yl)amino]-2-pyridinyl]-1,3-oxazinan-2-one | C₁₃H₁₄N₄O₂S | 43.95% |
Conditions
- Temperature
- 120 °C
Yield
- 44% of 3-[6-[(4-Methyl-1,3-thiazol-2-yl)amino]-2-pyridinyl]-1,3-oxazinan-2-one.
Procedure
Copied from the source record, unedited
**_September 21 2015_** 4-methylthiazol-2-amine (85 mg, 0.74 mmol), 3-(6-bromopyridin-2-yl)-1,3-oxazinan-2-one (191 mg, 0.74 mmol), 3-(6-bromopyridin-2-yl)-1,3-oxazinan-2-one (191 mg, 0.74 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (43.1 mg, 0.07 mmol) and cesium carbonate (291 mg, 0.89 mmol) in toluene (5 mL) were microwaved at 120 °C under N2 for one hour. LCMS showed no precursors and 51% of the desired mass MH+291 @ 0.86 min on a 2-min basic run. The reaction mixture was diluted with EtOAc, washed with water, filtered, and evaporated to give a brown solid as the crude product. The crude product was added to a Biotage column, and was eluted with 15-100%EtOAc in Heptane. Collected fractions. **_September 22 2015_** Based on TLC and LCMS, the product fractions w
The source
This record comes from experimental reaction archive (ord-db902466b4d9464996daff204ba92575). Open the source and check it against what is on this page.
experimental reaction archive record ord-db902466b4d9464996daff204ba92575 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.
Where to next
More Buchwald–Hartwig amination records
Other runs of this class, one page per distinct transformation.
Open in the Reaction Lab
The atom map, the bonds that break and form, and records running the same transformation.
Percent yield calculator
Work out a yield from what you isolated against what the equation allows.
Molecules A–Z
Every named molecule, with its identifiers and sources.