Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Triethylamine | HCID 8471 | — |
| Edukt | Tri-o-tolylphosphine | HCID 80271 | — |
| Edukt | 5-Bromo-4-methylpyridine-2-carbonitrile | HCID 53395468 | — |
| Edukt | HCID 178496569 | HCID 178496569 | — |
| Katalysator | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | HCID 178496566 | HCID 178496566 | 94% |
Reaktionsschritte
1-(((trans)-4-Methoxycyclohexyl)methyl)-7-(trimethylstannyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one (0.721 g, 1.64 mmol), 5-bromo-4-methylpicolinonitrile (0.323 g, 1.64 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.150 g, 0.164 mmol), triethylamine (0.687 mL, 4.93 mmol), tri-ortho-toylphosphine (0.100 g, 0.328 mmol) and dimethylformamide (8 mL) were combined in a sealed reaction vessel. Nitrogen was bubbled through the reaction for 5 min and reaction was heated at 100° C. for 3 h. Reaction is filtered, concentrated and purified by silica gel column chromatography (0-80% ethyl acetate in hexanes). Fractions were combined and concentrated to afford the crude title compound used directly for next step (0.607 g, 1.55 mmol, 94% yield). MS (ESI) m/z 393.5 [M+1]+.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US08507492B2 |
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| Quelldatensatz | uspto-grants-2013_08 |
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| ORD ID | ord-b7e453c4b2ba421bb75e90e08a47e936 |
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| Quellennotiz | uspto-grants-2013_08 |
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