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

HRID 2427964Notes

Reaction equation

HRID 2427964 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][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

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-9321ac506948483185ed0d9ba84a3c8f
Source dataset
uspto-grants-2011_06
Patent number
US07968556B2

Reaction notes

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