Sulfuric Acid → 2,4-Diaminopyrimidin-5-ol

HRID 1081640Notes

Reaction equation

HRID 1081640 reaction equation
S(=O)(=O)(O)O.S(O)([O:9][C:10]1[C:11]([NH2:17])=[N:12][C:13]([NH2:16])=[N:14][CH:15]=1)(=O)=O>O>[NH2:16][C:13]1[N:12]=[C:11]([NH2:17])[C:10]([OH:9])=[CH:15][N:14]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 19955491HCID 19955491, compound

Product 1

HCID 131268512,4-Diaminopyrimidin-5-olYield 114.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of 23.0 grams (0.235 mole) of concentrated sulfuric acid and about 18 mL of water was heated to reflux, and 48.5 grams (0.235 mole) of 2,4-diamino-5-pyrimidinyl hydrogen sulfate was added in one portion. Upon completion of addition, the reaction mixture was heated at reflux for ten minutes and then was immediately cooled in an ice-water bath. The resultant solid was collected by filtration, and the filter cake was washed with 100 mL of cold water. The solid was dried, yielding 34.0 grams of 2,4-diamino-5-hydroxypyrimidine hydrosulfate salt, mp 290° C., dec. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureto reflux
  2. additionUpon completion of addition
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux for ten minutes
  5. temperaturewas immediately cooled in an ice-water bath
  6. filtrationThe resultant solid was collected by filtration
  7. washthe filter cake was washed with 100 mL of cold water
  8. customThe solid was dried

Sources & evidence

ORD record
ord-5f72147e60be4f63ac18b04e4c7a801b
Source dataset
uspto-grants-1996_12
Patent number
US05587379

Reaction notes

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