Buchwald–Hartwig amination: 5-Bromopyrimidine → 3-(5-Pyrimidinylamino)benzenesulfonamide
19% yield, run at 130 °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 | 5-Bromopyrimidine | C₄H₃BrN₂ | |
| Reactant | Benzenesulfonamide, 3-amino- | C₆H₈N₂O₂S | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Dimethylacetamide | C₄H₉NO | |
| Product | 3-(5-Pyrimidinylamino)benzenesulfonamide | C₁₀H₁₀N₄O₂S | 18.77% |
Conditions
- Temperature
- 130 °C
Yield
- 19% of 3-(5-Pyrimidinylamino)benzenesulfonamide.
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
A mixture of 3-aminobenzenesulfonamide (110mg, 0.64 mmol), 5-bromopyrimidine (102 mg, 0.64 mmol),(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (29.6 mg, 0.05 mmol), diacetoxypalladium (5.74 mg, 0.03 mmol) and cesium carbonate (250 mg, 0.77 mmol) in degassed DMA (1.9 mL) was heated **_in the microwave_** for 35 min at 130°C. LC MS FLA-04665-12-01 (pH extract 6-7) showed some product. Reaction was stopped. Extraction with AE + ethanol / aq. sat NH4Cl (pH7), then back extraction with DCM.The organics were dried over MgSO4 and concentrated _in vacuo._ The crude product was adsorbed on silica gel 40-60µm and purified by flash chromatography on silica gel 15-40µm eluting with 3.5 % of ethanol in dichloromethane (NH3 0.5 %) to provide 3-(pyrimidin-5-ylamino)benzenesulfonamide (30.0
The source
This record comes from experimental reaction archive (ord-f980d50ac3ae43a58ddfe2efc500c048). Open the source and check it against what is on this page.
experimental reaction archive record ord-f980d50ac3ae43a58ddfe2efc500c048 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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