HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Potassium Carbonate → 5-Methyl-1-((R)-1-phenylethyl)-6-(quinolin-5-YL)-1H-imidazo[4,5-B]pyrazin-2(3H)-one
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Potassium Carbonate | HCID 11430 | — |
| Edukt | Quinolin-5-ylboronic acid | HCID 5153389 | — |
| Edukt | 5-Methyl-N2-((R)-1-phenylethyl)-6-(quinolin-5-yl)pyrazine-2,3-diamine | HCID 68853517 | — |
| Edukt | (R)-6-Bromo-5-methyl-N2-(1-phenylethyl)pyrazine-2,3-diamine | HCID 86626390 | — |
| Katalysator | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Lösungsmittel | Water | HCID 962 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | 5-Methyl-1-((R)-1-phenylethyl)-6-(quinolin-5-YL)-1H-imidazo[4,5-B]pyrazin-2(3H)-one | HCID 66699593 | 67% |
Reaktionsschritte
5-Methyl-N2-((R)-1-phenylethyl)-6-(quinolin-5-yl)pyrazine-2,3-diamine. (R)-6-Bromo-5-methyl-N2-(1-phenylethyl)pyrazine-2,3-diamine (0.534 g, 1.74 mmol), quinoline-5-boronic acid (0.331 g, 1.91 mmol), tetrakis(triphenylphosphine) palladium (0.20 g, 0.175 mmol), and potassium carbonate (0.96 g, 6.96 mmol) in water (4 mL) and dimethylformamide (15 mL) was reacted according to General Procedure B and purified via Biotage silica gel chromatography (0-10% methanol in dichloromethane, 40M column) and the resultant solid triturated with water/methanol to afford the title compound (0.42 g, 67% yield). MS (ESI) m/z 356.4 [M+1]+.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08372976B2 |
| Quelldatensatz | uspto-grants-2013_02 |
| ORD ID | ord-3b72cdb49a98408e944f5c4d37ed84e2 |
| Quellennotiz | uspto-grants-2013_02 |