Water → Tert-butyl (6-formyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate

HRID 2176691Notes

Reaction equation

HRID 2176691 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[N:10][N:11]=2)[N:8]=1)=C.O.I([O-])(=O)(=O)=[O:23].[Na+]>C1COCC1.[Os](=O)(=O)(=O)=O>[CH:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[N:10][N:11]=2)[N:8]=1)=[O:23]

Participants

6

Reactant 3

HCID 962WaterHCID 23667635Sodium periodateHCID 57691367Tert-butyl (6-vinyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate

Product 1

HCID 57691111Tert-butyl (6-formyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamateYield 72%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Tert-butyl (6-vinyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate (485 mg, 1.76 mmol) was dissolved in 5 mL of THF and 5 mL of water then osmium tetroxide (0.687 mL (4% water solution), 0.0176 mmol) was added and stirred for 5 min. Sodium periodate was added (141, 3.53 mmol) and the reaction was stirred for 2 h. The reaction was then extracted with dichloromethane (3×10 mL), dried over Na2SO4 and concentrated. Purification via MPLC (DCM/MeOH+1% NH4OH) afforded title compound as a tan solid (350 mg, 72% yield).

Workup

  1. stirringthe reaction was stirred for 2 h
  2. extractionThe reaction was then extracted with dichloromethane (3×10 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification via MPLC (DCM/MeOH+1% NH4OH)

Sources & evidence

ORD record
ord-f0b892c247ee4544a47e733c978116f6
Source dataset
uspto-grants-2015_06
Patent number
US09066954B2

Reaction notes

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