6-Amino-1,3-dimethyluracil → 6-Amino-1,3-dimethyl-5-nitrosouracil

HRID 858047

Reaction equation

HRID 858047 reaction equation
[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[N:5]([CH3:10])[C:4](=[O:11])[CH:3]=1.[N:12]([O-])=[O:13].[Na+]>O>[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[N:5]([CH3:10])[C:4](=[O:11])[C:3]=1[N:12]=[O:13]

Participants

4

Reactant 2

HCID 811526-Amino-1,3-dimethyluracilHCID 23668193Sodium Nitrite

Product 1

HCID 811336-Amino-1,3-dimethyl-5-nitrosouracil

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Commercially available 6-amino-1,3-dimethyl-1H-pyrimidine-2,4-dione (10 mmol) was dissolved in 1:1 water/glacial acetic acid (50 mL total volume) at 80° C. and sodium nitrite (20 mmol) added in portions. After the addition was complete the reaction mixture was stirred at 80° C. for 1 hr. Cooled in ice for 30 mins then filtered and washed with water. The precipitate was dried in vacuo to give crude 6-amino-1,3-dimethyl-5-nitroso-1H-pyrimidine-2,4-dione as a red-violet colored solid which was of sufficient purity for subsequent use without additional purification (89%).

Workup

  1. additionAfter the addition
  2. temperatureCooled in ice for 30 mins
  3. filtrationthen filtered
  4. washwashed with water
  5. customThe precipitate was dried in vacuo

Sources & evidence

ORD record
ord-f528c07c773b459ea5585eff18503e09
Source dataset
uspto-grants-2006_12
Patent number
US07148229B2

Linked notes

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