Ethanol → 2-(4-Hydroxyphenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide

HRID 391631Notes

Reaction equation

HRID 391631 reaction equation
[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][C:21]([OH:24])=[CH:20][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=CC([NH:37]C2N=C(C(OCC)=O)C([N+]([O-])=O)=C(NC3C=CC=CC=3OC)N=2)=CC=1.[CH2:61]([OH:63])C>[Pd]>[OH:24][C:21]1[CH:22]=[CH:23][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:19][CH:20]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 57474609Ethyl 2-(4-hydroxyphenylamino)-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylateHCID 57474610Ethyl 5-amino-2-(4-hydroxyphenylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate

Product 1

HCID 249379902-(4-Hydroxyphenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamideYield 98%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Ethyl 5-amino-2-(4-hydroxyphenylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate. Ethyl 2-(4-hydroxyphenylamino)-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate (220 mg, 0.517 mmol) was dissolved in ethanol (10 mL) and 10% palladium on carbon (55 mg, 0.052 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 (60-100% ethyl acetate in hexanes). Fractions containing product were combined and the solvent evaporated to provide the title compound (201.3 mg, 0.509 mmol, 98% yield). MS (ESI) m/z 396.2 [M+1]+.

Workup

  1. filtrationThe reaction was then filtered through Celite, solvent
  2. customwas removed under reduced pressure
  3. custompurified by column chromatography (60-100% ethyl acetate in hexanes)
  4. additionFractions containing product
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-e36868db4e5a4578b59058a54a930263
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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