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

HRID 391639
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 391639
[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]=[CH:20][C:19]=2[OH:24])=[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=CC=CC=1[NH:37]C1N=C(C(OCC)=O)C([N+]([O-])=O)=C(NC2C=CC=CC=2OC)N=1.[CH2:61]([OH:63])C>[Pd]>[OH:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[NH:17][C:5]1[N:6]=[C:7]2[C:2]([NH:1][C:61](=[O:63])[N:8]2[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[C:3]([C:25]([NH2:37])=[O:26])[N:4]=1
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Komponenten

5

Edukt 3

HCID 702EthanolHCID 57474630Ethyl 2-(2-hydroxyphenylamino)-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylateHCID 57474631Ethyl 5-amino-2-(2-hydroxyphenylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate

Produkt 1

HCID 249381082-(2-Hydroxyphenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamideAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

Ethyl 5-amino-2-(2-hydroxyphenylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate. Ethyl 2-(2-hydroxyphenylamino)-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate (362 mg, 0.851 mmol) was dissolved in ethanol (20 mL) and 10% palladium on carbon (91 mg, 0.085 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 (50% ethyl acetate in hexanes). Fractions containing product were combined and the solvent evaporated to provide the title compound (272.6 mg, 0.689 mmol, 81% 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 (50% ethyl acetate in hexanes)
  4. additionFractions containing product
  5. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-ba1ae769f7674b13ac3d0211c4ee58cf
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08383634B2

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