Buchwald–Hartwig amination: 2,4-Dichloropyrimidine → 2-Chloro-4-(1,2,3,4-tetrahydroquinolin-1-yl)pyrimidine
7% 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 | 2,4-Dichloropyrimidine | C₄H₂Cl₂N₂ | |
| Reactant | 1,2,3,4-Tetrahydroquinoline | C₉H₁₁N | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | 2-Chloro-4-(1,2,3,4-tetrahydroquinolin-1-yl)pyrimidine | C₁₃H₁₂ClN₃ | 7.28% |
Conditions
- Temperature
- 120 °C
Yield
- 7% of 2-Chloro-4-(1,2,3,4-tetrahydroquinolin-1-yl)pyrimidine.
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
2,4-dichloropyrimidine (200 mg, 1.34 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (78 mg, 0.13 mmol), Tris(dibenzylideneacetone)dipalladium(0) (61.5 mg, 0.07 mmol) and Cesium carbonate (656 mg, 2.01 mmol) was added to a microwave vial. toluene (2 mL) was added. 1,2,3,4-tetrahydroquinoline (179 mg, 1.34 mmol) was added. Heated to 120ºC in microwave oven for 90min. Crude filtered through celite and then added to prepHPLC. 30-70% acetonitrile in water. Pure fractions pooled and then freezedried over night. Yielded 1-(2-chloropyrimidin-4-yl)-1,2,3,4-tetrahydroquinoline (24.00 mg, 7.28 %)
The source
This record comes from experimental reaction archive (ord-4dd72fee5c294abbb8cdefc25f205782). Open the source and check it against what is on this page.
experimental reaction archive record ord-4dd72fee5c294abbb8cdefc25f205782 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.
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