HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 14Generated: October 23, 2026
4-Amino-3-methoxybenzaldehyde → 4-(5-Chloro-4-(imidazo[1,2-a]pyridin-3-yl)pyrimidin-2-ylamino)-3-methoxybenzaldehyde
https://huagongshe.com/en/reaction/14
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 4-Amino-3-methoxybenzaldehyde | HCID 19765052 | — |
| Reactant | 3-(2,5-Dichloropyrimidin-4-yl)imidazo[1,2-a]pyridine | HCID 46934605 | — |
| Reagent | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 4-(5-Chloro-4-(imidazo[1,2-a]pyridin-3-yl)pyrimidin-2-ylamino)-3-methoxybenzaldehyde | HCID 59291052 | 34.9% |
Reaction Steps
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-methoxybenzaldehyde (34.9 %) as a clear yellow solid. PBO-01132-77-02 w=2 g
Provenance & Evidence
| Source dataset | 750 AstraZeneca ELN dataset |
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| ORD ID | ord-4695ad3979554c448a445867cc030440 |
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| Source note | 750 AstraZeneca ELN dataset |
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