Hydrogen Peroxide → 2-(4-[1,2,3]Triazol-1-yl-butyl)-pyrimidin-5-ol

HRID 349229Notes

Reaction equation

HRID 349229 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][C:10]2[N:15]=[CH:14][C:13](B(O)O)=[CH:12][N:11]=2)[CH:5]=[CH:4][N:3]=[N:2]1.[OH2:19].OO>C1COCC1.[Cl-].[Na+].O>[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][C:10]2[N:15]=[CH:14][C:13]([OH:19])=[CH:12][N:11]=2)[CH:5]=[CH:4][N:3]=[N:2]1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 694862702-(4-[1,2,3]Triazol-1-yl-butyl)-pyrimidine-5-boronic acid

Product 1

HCID 694861582-(4-[1,2,3]Triazol-1-yl-butyl)-pyrimidin-5-ol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2-(4-[1,2,3]Triazol-1-yl-butyl)-pyrimidine-5-boronic acid (0.099 g, 0.40 mmol) is dissolved in THF (0.5 ml) and water (0.5 ml) and hydrogen peroxide (30 wt %) (0.054 g, 0.48 mmol) is added. After stirring the solution at r.t. for 2 h, brine (3 ml) is added and the mixture is extracted with THF (2×10 ml). The combined organic phases are dried over MgSO4 and concentrated in vacuo yielding 2-(4-[1,2,3]triazol-1-yl-butyl)-pyrimidin-5-ol as a off-white solid. Yield 85 mg (97%).

Workup

  1. extractionthe mixture is extracted with THF (2×10 ml)
  2. dry with materialThe combined organic phases are dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bfede6369c7d404c970ba5d0cf7bc4de
Source dataset
uspto-grants-2007_02
Patent number
US07179812B2

Reaction notes

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