Hydrochloric Acid → 6-amino-1-benzyl-5-nitrosopyrimidine-2,4(1H,3H)-dione

HRID 18120Notes

Reaction equation

HRID 18120 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6](=[O:15])[NH:5][C:4](=[O:16])[CH:3]=1.[N:17]([O-])=[O:18].[Na+].Cl>CN(C)C=O.O>[NH2:1][C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6](=[O:15])[NH:5][C:4](=[O:16])[C:3]=1[N:17]=[O:18]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2507466-Amino-1-benzyluracilHCID 23668193Sodium Nitrite

Product 1

HCID 33071146-amino-1-benzyl-5-nitrosopyrimidine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 6-amino-1-benzyl-1,3-dihydropyrimidine-2,4-dione (2.0 g, 9.2 mmol) in a mixture of 15 ml of N,N-dimethylformamide and 5 ml of water at 90° C. was added sodium nitrite (1.27 g, 69 mmol). To this reaction mixture was added concentrated hydrochloric acid until there was no deepening of color, and the mixture was heated at 70° C. for 1 hour. The solvent was removed under reduced pressure, the residue dissolved in water, and concentrated hydrochloric acid added to produce a pH of 4.0. The precipitate was filtered off, washed with water, and dried under reduced pressure, to provide 6-amino-5-nitroso-1-benzyl-1,3-dihydropyrimidine-2,4-dione, a compound of formula (24).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in water
  3. additionconcentrated hydrochloric acid added
  4. customto produce a pH of 4.0
  5. filtrationThe precipitate was filtered off
  6. washwashed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-a760c8ad32b94ef49706c123357fe924
Source dataset
uspto-grants-2010_06
Patent number
US07741331B2

Reaction notes

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