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

HRID 1779396Notes

Reaction equation

HRID 1779396 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 ((:).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-3b84394c84e348d0ad6604b7187e6f50
Source dataset
uspto-grants-1997_05
Patent number
US05627189

Reaction notes

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