HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
3-Aminophenol → 2-(3-Hydroxyphenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | 3-Aminophenol | HCID 11568 | — |
| Edukt | Diisopropylethylamine | HCID 81531 | — |
| Edukt | Ethyl 2-chloro-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate | HCID 57474573 | — |
| Edukt | Ethyl 2-(3-hydroxyphenylamino)-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate | HCID 57474601 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | 2-(3-Hydroxyphenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide | HCID 24937989 | 94% |
Reaktionsschritte
Ethyl 2-(3-hydroxyphenylamino)-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate. To a solution of ethyl 2-chloro-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate (See Example 30.A) (200 mg, 0.567 mmol) in DMF (3 mL) was added 3-aminophenol (74.3 mg, 0.680 mmol) and N,N-diisopropylethylamine (0.149 mL, 0.851 mmol). The reaction was stirred at room temperature overnight. Solvent was removed under reduced pressure and the resulting residue was purified by chromatography on a normal phase silica gel column (25-43% ethyl acetate in hexanes). Fractions containing product were combined and the solvent evaporated to provide the title compound (227 mg, 0.534 mmol, 94% yield) as an orange solid. MS (ESI) m/z 426.2 [M+1]+.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08383634B2 |
| Quelldatensatz | uspto-grants-2013_02 |
| ORD ID | ord-02ed0463418840f0be512fe9551ba0f7 |
| Quellennotiz | uspto-grants-2013_02 |