Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride | HCID 2734211 | — |
| Reactant | (1-Benzothiophen-3-yl)boronic acid | HCID 2776344 | — |
| Reactant | 4-(2-((2-Chloro-9-isopropyl-9H-purin-6-yl)amino)ethyl)phenol | HCID 75529970 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Product | Lhd-221 | HCID 46199207 | — |
Reaction Steps
A flame-dried schlenk flask was charged with 4-(2-(2-chloro-9-isopropyl-9H-purin-6-ylamino)ethyl)phenol (0.62 mmol), thianaphthene-3-boronic acid (0.94 mmol), pd2(dba)3 (0.062 mmol), Cs2CO3 (1.25 mmol) and 1,3-bis(2,4,6-trimethylphenyl) imidazolium chloride (0.125 mmol). The flask was evacuated and backfilled with N2 and anhydrous 1,4-dioxane (2 mL) was added. The flask was sealed and the reaction mixture was stirred at 80° C. for 24 hours. The reaction mixture was concentrated and purified directly by column chromatography on silica gel, eluting with hexane/EtOAc (20:1 to 1:4) to afford the title compound as a yellowish solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08927281B2 |
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| Source dataset | uspto-grants-2015_01 |
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| ORD ID | ord-0aa1cb5c8d2c48a5b5b79c12fef42d4b |
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| Source note | uspto-grants-2015_01 |
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