Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-(Methylcarbamoyl)benzeneboronic acid | HCID 2773526 | — |
| Reactant | 2,4-dichloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo(2,3-d)pyrimidine | HCID 86679621 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86726509 | HCID 86726509 | 68% |
Reaction Steps
2,4-Dichloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (1 equiv), (4-(methylcarbamoyl)phenyl)boronic acid (1.2 equiv), sodium carbonate (3 equiv) and [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) complex with dichloromethane (0.1 equiv) were combined in a 5:1 mixture of 1,4-dioxane and water (0.27 M). The mixture was heated to 90° C. for 3 h. The crude product was purified on silica gel (0-100% ethyl acetate in hexane) to give the title compound (68% yield) an orange solid. MS (ESI) m/z 451.2 [M]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09428509B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-d6b96ef7e74746b9b0cc24dcfb1d8dab |
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| Source note | uspto-grants-2016_08 |
|---|