Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Methane | HCID 297 | — |
| Edukt | O-Phenylenediamine | HCID 7243 | — |
| Edukt | Triethylamine | HCID 8471 | — |
| Edukt | Diethyl cyanophosphonate | HCID 76257 | — |
| Edukt | 3-Amino-6-bromopyrazine-2-carboxylic acid | HCID 18521600 | — |
| Lösungsmittel | Water | HCID 962 | — |
| Lösungsmittel | 1,2-Dimethoxyethane | HCID 8071 | — |
| Lösungsmittel | Ethyl Acetate | HCID 8857 | — |
| Produkt | HCID 52937760 | HCID 52937760 | 60,4% |
Reaktionsschritte
A mixture of 3-amino-6-bromo-pyrazine-2-carboxylic acid (10 g, 45.87 mmol), benzene-1,2-diamine (5.45 g, 50.46 mmol), diethoxyphosphorylformonitrile (8.23 g, 50.46 mmol) and triethylamine (12.79 mL, 91.74 mmol) in DME (30 mL) was heated in the microwave at 170° C. for 40 minutes. The mixture was allowed to cool and water was added. The resultant dark-coloured precipitate was dissolved in EtOAc and stirred with charcoal for 30 minutes. After filtering through celite, the filtrate was concentrated in vacuo to give the product as a yellow solid (8.04 g, 60% Yield). 1H NMR (400 MHz, DMSO) 7.22-7.32 (2H, m), 7.55 (1H, d), 7.75 (1H, d), 7.8 (1 h, br s), 8.8 (1H, br s), 13.1 (1H, s); MS (ES+) 291
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US08841308B2 |
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| Quelldatensatz | uspto-grants-2014_09 |
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| ORD ID | ord-3098fade2ad445e28fe562e67f568c00 |
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| Quellennotiz | uspto-grants-2014_09 |
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