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
57% yield, run at 115 °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 | 57.15% |
Conditions
- Temperature
- 115 °C
Yield
- 57% of 3-[6-[(4-Methyl-1,3-thiazol-2-yl)amino]-2-pyridinyl]-1,3-oxazinan-2-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 28 2015_** 4-methylthiazol-2-amine (300 mg, 2.63 mmol), 3-(6-bromopyridin-2-yl)-1,3-oxazinan-2-one (676 mg, 2.63 mmol), 3-(6-bromopyridin-2-yl)-1,3-oxazinan-2-one (676 mg, 2.63 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (152 mg, 0.26 mmol) and cesium carbonate (1027 mg, 3.15 mmol) in toluene (13 mL)/DMF (2.00 mL) were microwaved at 115 °C under N2 for one hour. (Note: Based on the observation in EN07946-41, _DMF was added to improve the heating due to the low thremal absorbance of toluene.)_ One hour later, LCMS showed 13% of the precursor MH+257/259 @ 0.84 min and 36% of the desired mass MH+291 @ 0.86 min along with some unknowns on a 2-min basic run. The reaction seemed not complete. The reaction was microwaved at 115 °C for another 45 min. One hou
The source
This record comes from experimental reaction archive (ord-afb4a5c3ac0340ae885e81e91d7c667d). Open the source and check it against what is on this page.
experimental reaction archive record ord-afb4a5c3ac0340ae885e81e91d7c667d 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
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