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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

80% yield, run at 115 °C, as recorded by experimental reaction archive. The written procedure is below.

verified record, 80% yield recorded, Not balanced as written, From experimental reaction archive

Reagents, catalysts and solvents are in the table below.

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The atoms, from reactants to products

CCCSCNCCCCCNCCOCCONNBr
Reactants · 1/6
breakingformingbond order changesmapped atom that changes

Drawn from the record's atom map: which bonds break and which form between the reactants and products the source listed. It shows a change in connectivity, not a simulated trajectory and not a mechanism.

What was in the flask

RoleSpeciesFormulaYield
Reactant4-(6-Bromo-2-pyridinyl)morpholin-3-oneC₉H₉BrN₂O₂—
Reactant2-Amino-4-methylthiazoleC₄H₆N₂S—
ReagentCesium carbonateCCs₂O₃—
Catalyst1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)C₃₉H₃₂OP₂—
Catalyst(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumC₃₄H₂₈O₂Pd—
SolventTolueneC₇H₈—
Product4-[6-[(4-Methyl-1,3-thiazol-2-yl)amino]-2-pyridinyl]morpholin-3-oneC₁₃H₁₄N₄O₂S80.02%

The equation does not balance as written. That is usual for an experimental record: the source listed what it put in and what it measured, not a stoichiometric equation.

Conditions

Temperature
115 °C

Only the dimensions the source stated are listed. Anything absent here was not recorded, and it is not inferred from what the class usually needs.

Yield

  • 80% of 4-[6-[(4-Methyl-1,3-thiazol-2-yl)amino]-2-pyridinyl]morpholin-3-one.

Procedure

Copied from the source record, unedited

**_September 24 2015_** 4-methylthiazol-2-amine (200 mg, 1.75 mmol), 4-(6-bromopyridin-2-yl)morpholin-3-one (450 mg, 1.75 mmol), 4-(6-bromopyridin-2-yl)morpholin-3-one (450 mg, 1.75 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (81 mg, 0.14 mmol) and cesium carbonate (685 mg, 2.10 mmol) in toluene (15 mL) and DMF (1)were microwaved at 115 °C under N2 for one hour. _(Note: Initially, DMF was not added as co-solvent, the microwave instrument was repeatly failed to reach the temperature, and shut down ar 100 °C. It was due to the low thremal absorbance of toluene. Therefore, DMF was added to improve this situation.)_ LCMS showed no precursors and 87% of the desired mass MH+291 @ 0.87 min on a 2-min basic run. The reaction was cooled to RT. **_September 25 2015_** The

The source

This record comes from experimental reaction archive (ord-4ad2f7e2a41645bd9dba54aaef4fa989). Open the source and check it against what is on this page.

  • experimental reaction archive record ord-4ad2f7e2a41645bd9dba54aaef4fa989 from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.

    experimental record · quality medium · source

experimental reaction record.

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

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