Hydrogen Peroxide → HCID 178492094, compound

HRID 1262420Notes

Reaction equation

HRID 1262420 reaction equation
[OH:1]O.[CH3:3][O:4][C:5]1[C:6]([C:11]2[N:19]3[C:14]([CH:15]=[N:16][C:17](SC)=[N:18]3)=[CH:13][CH:12]=2)=[N:7][CH:8]=[CH:9][CH:10]=1.[OH-].[Na+].O>CO.O.O.[O-][W]([O-])(=O)=O.[Na+].[Na+].C(O)(=O)C>[CH3:3][O:4][C:5]1[C:6]([C:11]2[N:19]3[C:14]([CH:15]=[N:16][C:17]([OH:1])=[N:18]3)=[CH:13][CH:12]=2)=[N:7][CH:8]=[CH:9][CH:10]=1

Participants

8

Reactant 4

HCID 784Hydrogen Peroxide2×HCID 962WaterHCID 14798Sodium HydroxideHCID 667127347-(3-Methoxy-pyridin-2-yl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 178492094HCID 178492094, compoundYield 85.8%

Reagents, catalysts & solvents 3

HCID 150191Sodium Tungstate DihydrateCatalystHCID 176Acetic AcidSolvent2×HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Sodium Tungstate Dihydrate (23.0 mg, 0.0698 mmol) and 50% Hydrogen Peroxide (50:50, Hydrogen peroxide:Water, 0.150 mL, 2.64 mmol) were added to 7-(3-Methoxy-pyridin-2-yl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (0.190 g, 0.698 mmol) in Methanol (10.0 mL) and Acetic acid (0.400 mL, 7.04 mmol). The mixture was stirred at 50° C. Formation of the sulfoxide was evident, followed by formation of the sulfone. After o.n., a 1:1 mixture of sulfoxide:sulfone was present. Additional 50% Hydrogen Peroxide (50:50, Hydrogen peroxide:Water, 0.150 mL, 2.64 mmol) was added. Further heating gave a ˜2:1 mixture. Aqueous workup (10% Na2S2O3, NaHCO3, water) and extract with DCM. The crude sulfone:sulfoxide mixture was hydrolyzed by dissolving in Tetrahydrofuran (6.0 mL) and adding 5.0 M of Sodium hydroxide in Water (0.500 mL, 2.50 mmol), then heating at 50° C. for 6 h. Work up by acidifying with Acetic acid to pH 5-6. Partition between DCM and water, extract with DCM using MeOH to solubilize the ppt that forms during extraction. Dry and conc. in vacuo to afford 7-(3-Methoxy-pyridin-2-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-ol (145 mg, 85%).

Workup

  1. temperatureFurther heating
  2. customgave a ˜2:1 mixture
  3. extractionAqueous workup (10% Na2S2O3, NaHCO3, water) and extract with DCM
  4. dissolutionby dissolving in Tetrahydrofuran (6.0 mL)
  5. temperatureheating at 50° C. for 6 h
  6. customPartition between DCM and water
  7. extractionextract with DCM
  8. extractionforms during extraction
  9. customDry and conc. in vacuo

Sources & evidence

ORD record
ord-193db836c391466da80949489a60e89a
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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