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

HRID 2250339Notes

Reaction equation

HRID 2250339 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-d1e3892fb5754b7a955d212edc17d55f
Source dataset
uspto-grants-2008_01
Patent number
US07317017B2

Reaction notes

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