Uracil → 5-Nitrosouracil

HRID 1888927

Reaction equation

HRID 1888927 reaction equation
N[C:2]1[NH:7][C:6](=[O:8])[NH:5][C:4](=[O:9])[CH:3]=1.N1C=CC(=O)NC1=O.[N:18]([O-])=[O:19].[Na+]>C(O)(=O)C.O>[N:18]([C:3]1[C:4](=[O:9])[NH:5][C:6](=[O:8])[NH:7][CH:2]=1)=[O:19]

Participants

6

Reactant 3

HCID 1174UracilHCID 701206-AminouracilHCID 23668193Sodium Nitrite

Product 1

HCID 3283635-NitrosouracilYield 132%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
10 °C

Procedure

1-Propyl, 3-cyclopropyl, 6-aminouracil (2) (12.8 g, 61.2 mmol) was dissolved in acetic acid (25 ml) in 200 ml of water and the mixture was cooled to 10° C. To the uracil solution, NaNO2 (7.6 g, 110.1 mmol) in 50 ml of water was added dropwise at 10° C. The mixture was stirred at 10° C. for 30 min and then at room temperature for 1 h. The solvent was removed under reduced pressure and the residue was dissolved in the mixture of absolute ethanol and CH2Cl2 (1:1) and boiled for 20 min. The hot mixture was filtered through a layer of Celite 545 to remove the insoluble inorganic salts. The mother liquid was evaporated under reduced pressured to remove the solvent to give 1-propyl, 3-cyclopropyl, 6-amino, 5-nitrosouracil (4) (11.4 g, 78%).

Workup

  1. waitat room temperature for 1 h
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in the mixture of absolute ethanol and CH2Cl2 (1:1)
  4. waitboiled for 20 min
  5. filtrationThe hot mixture was filtered through a layer of Celite 545
  6. customto remove the insoluble inorganic salts
  7. customThe mother liquid was evaporated
  8. customto remove the solvent

Sources & evidence

ORD record
ord-8f04e0512ca8496cbdde9403629e4db6
Source dataset
uspto-grants-2013_08
Patent number
US08501941B2

Linked notes

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