Methanol → 5-hydroxyiminomethyl-2,4(1H,3H)-pyrimidinedione

HRID 342529Notes

Reaction equation

HRID 342529 reaction equation
[O:1]=[C:2]1[NH:7][C:6](=[O:8])[C:5]([CH:9]=O)=[CH:4][NH:3]1.CO.Cl.[NH2:14][OH:15].C([O-])(=O)C.[K+]>O>[OH:15][N:14]=[CH:9][C:5]1[C:6](=[O:8])[NH:7][C:2](=[O:1])[NH:3][CH:4]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 3045905-FormyluracilHCID 443297Hydroxyamine hydrochlorideHCID 517044Potassium Acetate

Product 1

HCID 2687545-hydroxyiminomethyl-2,4(1H,3H)-pyrimidinedioneYield 84.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 2,4-dioxo-5(1H,3H)-pyrimidinecarbaldehyde (1.79 g, 12.8 mmol), methanol (35 mL) and water (35 mL) was heated at reflux and then a mixture of hydroxylamine hydrochloride (905 mg, 13 mmol), potassium acetate (1.28 g, 13 mmol) and water (15 mL) was added. The mixture was cooled and the solids were collected, washed with water and recrystallized from water/methanol to give 5-hydroxyiminomethyl-2,4(1H,3H)-pyrimidinedione (1.68 g, 10.8 mmol).

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. additionwas added
  4. temperatureThe mixture was cooled
  5. customthe solids were collected
  6. washwashed with water
  7. customrecrystallized from water/methanol

Sources & evidence

ORD record
ord-9daea01fac404099a7b44f2c4722b096
Source dataset
uspto-grants-1999_01
Patent number
US05859014

Reaction notes

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