Ethanol → 2-(3-Hydroxyphenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide

HRID 2427964Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2427964
[NH2:1][C:2]1[C:3]([C:25](OCC)=[O:26])=[N:4][C:5]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=2)=[N:6][C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16].OC1C=C([NH:37]C2N=C(C(OCC)=O)C([N+]([O-])=O)=C(NC3C=CC=CC=3OC)N=2)C=CC=1.[CH2:61]([OH:63])C>[Pd]>[OH:24][C:20]1[CH:19]=[C:18]([NH:17][C:5]2[N:6]=[C:7]3[C:2]([NH:1][C:61](=[O:63])[N:8]3[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][CH3:16])=[C:3]([C:25]([NH2:37])=[O:26])[N:4]=2)[CH:23]=[CH:22][CH:21]=1

Komponenten

5

Edukt 3

HCID 702EthanolHCID 57474601Ethyl 2-(3-hydroxyphenylamino)-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylateHCID 57474602Ethyl 5-amino-2-(3-hydroxyphenylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate

Produkt 1

HCID 249379892-(3-Hydroxyphenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamideAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

Ethyl 5-amino-2-(3-hydroxyphenylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate. Ethyl 2-(3-hydroxyphenylamino)-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate (227 mg, 0.534 mmol) was dissolved in ethanol (15 mL) and 10% palladium on carbon (56.8 mg, 0.053 mmol) was added. The reaction mixture was stirred at room temperature under an atmosphere of hydrogen overnight. The reaction was then filtered through Celite, solvent was removed under reduced pressure and purified by column chromatography (2% methanol in methylene chloride). A second chromatographic purification was necessary (50% ethyl acetate in hexanes). Fractions containing product were combined and the solvent evaporated to provide the title compound (186.8 mg, 0.472 mmol, 89% yield). MS (ESI) m/z 396.2 [M+1]+.

Aufarbeitung

  1. filtrationThe reaction was then filtered through Celite, solvent
  2. customwas removed under reduced pressure
  3. custompurified by column chromatography (2% methanol in methylene chloride)
  4. customA second chromatographic purification
  5. additionFractions containing product
  6. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-9321ac506948483185ed0d9ba84a3c8f
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07968556B2

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