HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 42004Generated: October 26, 2026
Cesium carbonate → Methyl 2-(2-chloropyrimidin-5-ylamino)-5-cyclopropylbenzoate
https://huagongshe.com/reaction/42004
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 5-Bromo-2-chloropyrimidine | HCID 606665 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | Methyl 2-amino-5-cyclopropylbenzoate | HCID 13052309 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | Methyl 2-(2-chloropyrimidin-5-ylamino)-5-cyclopropylbenzoate | HCID 86657256 | — |
Reaction Steps
In a schlenck tube, a mixture of methyl 2-amino-5-cyclopropylbenzoate (described in Intermediate 8 (step A) (26.15 mmol, 5 g), 5-bromo-2-chloropyrimidine (26.93 mmol, 5.21 g), Xantphos (1.07 mmol, 0.6 g), Pd2(dba)3 (1.07 mmol, 0.6 g) and Cs2CO3 (36.65 mmol, 11.9 g) in dioxane (210 ml) was heated at 100° C. overnight. Water and ethyl acetate were added to the reaction crude. The aqueous phase was extracted again with more ethyl acetate. The organic phase was washed with water and brine, dried, filtered and concentrated in vacuo. The crude mixture was purified by reverse chromatography (Water: MeOH/AcN 1:1 from 0% to 100%) affording 6 g (60% of yield) of the expected product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08536165B2 |
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| Source dataset | uspto-grants-2013_09 |
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| ORD ID | ord-185bb4a960824d82a53d420aa849be0a |
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| Source note | uspto-grants-2013_09 |
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