Ammonia → 1-(4-Aminophenyl)pyrimidine-2,4(1H,3H)-dione

HRID 18535

Reaction equation

HRID 18535 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:15]=[CH:14][C:13](=[O:16])[NH:12][C:11]2=[O:17])=[CH:6][CH:5]=1)([O-])=O.N.[H][H]>CO.[Ni]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:15]=[CH:14][C:13](=[O:16])[NH:12][C:11]2=[O:17])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 112763381-(4-Nitrophenyl)pyrimidine-2,4-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 670121351-(4-Aminophenyl)pyrimidine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of 1.4 g 1-(4-Nitro-phenyl)-1H-pyrimidine-2,4-dione in 120 mL MeOH, 15 g Raney Nickel (washed three times with MeOH) were introduced under a nitrogen atmosphere. Then 15 mL of a 7 M solution of NH3 in MeOH were added. The nitrogen atmosphere was replaced by a hydrogen atmosphere and the mixture was hydrogenated under normal pressure at RT. After 2 h the reaction mixture was filtered through a pad of celite. The solvents were removed under reduced pressure and the residue was subjected to the next reaction step without further purification. Yield: 502 mg.

Workup

  1. customwas hydrogenated under normal pressure at RT
  2. filtrationAfter 2 h the reaction mixture was filtered through a pad of celite
  3. customThe solvents were removed under reduced pressure
  4. customthe residue was subjected to the next reaction step without further purification

Sources & evidence

ORD record
ord-74c37d52c2334b12bb37a8433b13fbdd
Source dataset
uspto-grants-2010_06
Patent number
US07741341B2

Linked notes

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