HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Potassium Carbonate → 5-Methyl-1-((S)-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-((S)-1-phenylethyl)-6-(quinolin-5-yl)pyrazine-2,3-diamine | HCID 68853693 | — |
| Edukt | (S)-6-bromo-5-methyl-N2-(1-phenylethyl)pyrazine-2,3-diamine | HCID 86626389 | — |
| Katalysator | HCID 178418397 | HCID 178418397 | — |
| Lösungsmittel | Water | HCID 962 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | 5-Methyl-1-((S)-1-phenylethyl)-6-(quinolin-5-YL)-1H-imidazo[4,5-B]pyrazin-2(3H)-one | HCID 24985025 | 18% |
Reaktionsschritte
5-Methyl-N2-((S)-1-phenylethyl)-6-(quinolin-5-yl)pyrazine-2,3-diamine. A solution of (S)-6-bromo-5-methyl-N2-(1-phenylethyl)pyrazine-2,3-diamine (0.975 g, 3.19 mmol), quinoline-5-boronic acid (0.606 g, 3.50 mmol), tetrakis(triphenylphosphine)palladium (0.368 g, 0.319 mmol), and potassium carbonate (1.76 g, 12.76 mmol) in water (8 mL) and dimethylformamide (30 mL) was reacted according to General Procedure B and purified via Biotage silica gel chromatography (0-10% methanol in dichloromethane, 40M column). The resultant solid was triturated with water/methanol to afford the title compound (0.200 g, 18% yield). MS (ESI) m/z 356.5 [M+1]+.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08372976B2 |
| Quelldatensatz | uspto-grants-2013_02 |
| ORD ID | ord-51bc88db9e3e4e33a1ae6d8260220258 |
| Quellennotiz | uspto-grants-2013_02 |