Methanol → HCID 18375967, compound

HRID 2300827Notes

Reaction equation

HRID 2300827 reaction equation
[CH2:1]([S:3][C:4]1[N:9]=[C:8]([N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]=[CH:11]2)[C:7]([CH3:19])=[CH:6][N:5]=1)[CH3:2].CO.S([O-])(O[O-])(=O)=[O:23].[K+].[K+].[OH2:30]>>[CH2:1]([S:3]([C:4]1[N:9]=[C:8]([N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]=[CH:11]2)[C:7]([CH3:19])=[CH:6][N:5]=1)(=[O:23])=[O:30])[CH3:2]

Participants

5

Reactant 4

HCID 887MethanolHCID 962Water2×HCID 10313463Potassium peroxymonosulphateHCID 18375485HCID 18375485, compound

Product 1

HCID 18375967HCID 18375967, compound

Procedure

To a solution of 2-Ethylthio-4-(benzimidazol-1-yl)-5-methylpyrimidine (127.5 mg, 0.47 mmol) in methanol (1.2 mmol) at 0° C. was added slurry of potassium peroxymonosulfate (Oxone®) (870 mg, 1.41 mmol) in H2O (1.2 mL). The mixture was stirred at room temperature for 4 h, and was then diluted with H2O. The aqueous layer was extracted with CH2Cl2, and the combined organic layer was washed with H2O followed by brine. The organic extract was dried over Na2SO4 then purified (20 mg of crude material) by preparative thin layer chromatography eluting with 1:1 acetone:hexane system to give the title compound. Mass spectrum 303 (ESI, M+1).

Workup

  1. extractionThe aqueous layer was extracted with CH2Cl2
  2. washthe combined organic layer was washed with H2O
  3. extractionThe organic extract
  4. dry with materialwas dried over Na2SO4
  5. customthen purified (20 mg of crude material) by preparative thin layer chromatography
  6. washeluting with 1:1 acetone

Sources & evidence

ORD record
ord-be3e0df372834caa8b33be8206bf6cd6
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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