Acetic Acid → HCID 178508812, compound

HRID 1784110Notes

Reaction equation

HRID 1784110 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[C:4]([NH2:9])[N:3]=1.C(O)(=O)C.[N:14]([O-])=[O:15].[Na+]>O>[NH2:1][C:2]1[N:7]=[C:6]([OH:8])[C:5]([N:14]=[O:15])=[C:4]([NH2:9])[N:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 23668193Sodium NitriteHCID 178507952HCID 178507952, compound

Product 1

HCID 178508812HCID 178508812, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of 2,6-diamino-4-hydroxypyrimidine (12.9 g, 102.2 mmoles) in 200 ml of a 10% acetic acid solution in water at 80° C. was added dropwise a solution of NaNO2 (7.05 g, 102.2 mmoles) in 20 ml water. A pink precipitate was formed, which was further stirred for 1 hour at 80° C. The reaction mixture was cooled down in the refrigerator overnight. The precipitate was filtered off and dried over P2O5, providing the title compound as a pink powder (15.43 g, yield: 97%). The spectral data are in accordance with literature data (Landauer et al. in J. Chem. Soc. (1953) 3721-3722).

Workup

  1. customA pink precipitate was formed
  2. temperatureThe reaction mixture was cooled down in the refrigerator overnight
  3. filtrationThe precipitate was filtered off
  4. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-3c88173537034105b7659e892ebb0d18
Source dataset
uspto-grants-2009_03
Patent number
US07501513B2

Reaction notes

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