HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Aminophenol → 2-(2-Hydroxyphenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Aminophenol | HCID 5801 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Ethyl 2-chloro-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate | HCID 57474573 | — |
| Reactant | Ethyl 2-(2-hydroxyphenylamino)-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate | HCID 57474630 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-(2-Hydroxyphenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide | HCID 24938108 | 100% |
Reaction Steps
Ethyl 2-(2-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) (300 mg, 0.851 m mol) in DMF (5 mL) was added 2-aminophenol (111 mg, 1.021 mmol) and N,N-diisopropylethylamine (0.223 mL, 1.276 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 (50% ethyl acetate in hexanes). Fractions containing product were combined and the solvent evaporated to provide the title compound (362 mg, 0.851 mmol, 100% yield). MS (ESI) m/z 426.2 [M+1]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07968556B2 |
| Source dataset | uspto-grants-2011_06 |
| ORD ID | ord-618e07e4e1df41b6896fc45a9dffefb3 |
| Source note | uspto-grants-2011_06 |