Buchwald–Hartwig amination: 4-(6-Bromo-2-pyridinyl)morpholin-3-one → 4-[6-[(4-Methyl-1,3-thiazol-2-yl)amino]-2-pyridinyl]morpholin-3-one
67% 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 | 4-(6-Bromo-2-pyridinyl)morpholin-3-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 | 4-[6-[(4-Methyl-1,3-thiazol-2-yl)amino]-2-pyridinyl]morpholin-3-one | C₁₃H₁₄N₄O₂S | 66.55% |
Conditions
- Temperature
- 120 °C
Yield
- 67% of 4-[6-[(4-Methyl-1,3-thiazol-2-yl)amino]-2-pyridinyl]morpholin-3-one.
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
**_September 16 2015_** 4-methylthiazol-2-amine (65 mg, 0.57 mmol), 4-(6-bromopyridin-2-yl)morpholin-3-one (146 mg, 0.57 mmol), 4-(6-bromopyridin-2-yl)morpholin-3-one (146 mg, 0.57 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (26.4 mg, 0.05 mmol) and cesium carbonate (223 mg, 0.68 mmol) in toluene (5 mL) were microwaved at 120 °C under N2 for one hour. LCMS showed no precursors and 68% of the desired mass MH+291 @ 0.87 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. **_September 17 2015_** The crude product was added to a Biotage column, and was eluted with 0-10% ammoniated MeOH in DCM. Collected fractions. Based on TLC and LCMS, the product fractions we
The source
This record comes from experimental reaction archive (ord-3571e003ae98463b83eba103dff01204). Open the source and check it against what is on this page.
experimental reaction archive record ord-3571e003ae98463b83eba103dff01204 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
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