2-(Methylthio)pyrimidin-4-amine → 4-Amino-2-methylsulphinylpyrimidine

HRID 2291344Notes

Reaction equation

HRID 2291344 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[NH2:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([S:14][CH3:15])[N:9]=1>O>[NH2:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([S:14]([CH3:15])=[O:2])[N:9]=1

Participants

4

Reactant 2

HCID 2592252-(Methylthio)pyrimidin-4-amineHCID 23667635Sodium periodate2×

Product 1

HCID 212797904-Amino-2-methylsulphinylpyrimidineYield 89.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Sodium metaperiodate (1.3 g.) in water (5 ml.) was added to a solution of 4-amino-2-methylthiopyrimidine (0.7 g.) in water (10 ml.) at 90°, and the solution kept at 90° for 1 hour. A further 1.3 g. of sodium metaperiodate was added and the solution heated a further 0.5 hours and then cooled to room temperature. The mixture was filtered and the filtrate evaporated to dryness. The residue was triturated with MeOH and the suspension filtered and then the filtrate was evaporated to dryness. The residue was triturated with acetonitrile and the insoluble solid collected to give 4-amino-2-methylsulphinylpyrimidine (0.7 g.) which was used without further purification.

Workup

  1. temperaturethe solution heated a further 0.5 hours
  2. filtrationThe mixture was filtered
  3. customthe filtrate evaporated to dryness
  4. customThe residue was triturated with MeOH
  5. filtrationthe suspension filtered
  6. customthe filtrate was evaporated to dryness
  7. customThe residue was triturated with acetonitrile
  8. customthe insoluble solid collected

Sources & evidence

ORD record
ord-d4e286e222ab4cea98f1ae29494c2a8a
Source dataset
uspto-grants-1989_01
Patent number
US04795755

Reaction notes

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