Buchwald–Hartwig amination: 3-(2,5-Dichloropyrimidin-4-yl)imidazo[1,2-a]pyridine → 4-(5-Chloro-4-(imidazo[1,2-a]pyridin-3-yl)pyrimidin-2-ylamino)-3-methoxybenzaldehyde
35% 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 | 3-(2,5-Dichloropyrimidin-4-yl)imidazo[1,2-a]pyridine | C₁₁H₆Cl₂N₄ | |
| Reactant | 4-Amino-3-methoxybenzaldehyde | C₈H₉NO₂ | |
| Reagent | 1,8-Diazabicyclo(5.4.0)undec-7-ene | C₉H₁₆N₂ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | 4-(5-Chloro-4-(imidazo[1,2-a]pyridin-3-yl)pyrimidin-2-ylamino)-3-methoxybenzaldehyde | C₁₉H₁₄ClN₅O₂ | 34.9% |
Conditions
- Temperature
- 120 °C
Yield
- 35% of 4-(5-Chloro-4-(imidazo[1,2-a]pyridin-3-yl)pyrimidin-2-ylamino)-3-methoxybenzaldehyde.
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
3-(2,5-dichloropyrimidin-4-yl)imidazo[1,2-a]pyridine (4 g, 15.09 mmol), 4-amino-3-methoxybenzaldehyde (2.281 g, 15.09 mmol), 9,9-DIMETHYL-4,5-BIS(DIPHENYLPHOSPHINO)XANTHENE (0.873 g, 1.51 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM (0.345 g, 0.38 mmol) and 1,8-DIAZABICYCLO [5.4.0] UNDEC-7-ENE (5.64 ml, 37.72 mmol) were dissolved in Dioxane (120 ml) then degazed and purged with argon. The reaction was heated to reflux (bath 120°C) for 2H30. Reaction mixture was filtered through a filter cup and concentrated. FR01132-77-01 w=14.65 g The crude product was purified by flash chromatography (NOVASEP) on silica gel ( 15-40µm ) eluting with 0 to 5% methanol in dichloromethane. The solvent was evaporated to dryness to afford 4-(5-chloro-4-(imidazo[1,2-a]pyridin-3-yl)pyrimidin-2-ylamino)-3-metho
The source
This record comes from experimental reaction archive (ord-4695ad3979554c448a445867cc030440). Open the source and check it against what is on this page.
experimental reaction archive record ord-4695ad3979554c448a445867cc030440 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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