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

HRID 2427974Notes

Reaction equation

HRID 2427974 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]=[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

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-64a6d278ccea46ecb24cbf116e27b252
Source dataset
uspto-grants-2011_06
Patent number
US07968556B2

Reaction notes

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