Hydrogen Peroxide → 4-(1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenol

HRID 1641063Notes

Reaction equation

HRID 1641063 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[C:19]4=[N:20][CH:21]=[N:22][CH:23]=[C:18]4[CH:17]=[N:16]3)=[CH:11][CH:10]=2)O1.[OH-:25].[Na+].OO>C1COCC1>[N:15]1([C:12]2[CH:13]=[CH:14][C:9]([OH:25])=[CH:10][CH:11]=2)[C:19]2=[N:20][CH:21]=[N:22][CH:23]=[C:18]2[CH:17]=[N:16]1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 594187721-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 594187194-(1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The title compound 4-(1H-pyrazolo[3,4-d]-pyrimidin-1-yl)phenol (22) was prepared by the following procedure: To a solution of 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidine (22C) (100 mg, 0.31 mmol) in THF (5 mL) was added NaOH (0.248 mL, 0.621 mmol) and hydrogen peroxide (0.048 mL, 0.466 mmol). The mixture was stirred at 0° C. for 30 minutes The reaction mixture was concentrated and the residue was dissolved water (8 mL). The aqueous solution was acidified with diluted HCl. The white precipitate was collected, washed with water and dried to provide the title compound 4-(1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenol (22): 1H NMR (400 MHz, DMSO-D6) δ ppm 9.75 (1H, s), 9.44 (1H, s), 9.09 (1H, s), 8.59 (1H, s), 7.82-7.99 (2H, m), 6.83-7.05 (2H, m).

Workup

  1. customThe title compound 4-(1H-pyrazolo[3,4-d]-pyrimidin-1-yl)phenol (22) was prepared by the following procedure
  2. concentrationwas concentrated
  3. dissolutionthe residue was dissolved water (8 mL)
  4. customThe white precipitate was collected
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-067950fd5ef948ca94e9b6c3b2f35fff
Source dataset
uspto-grants-2012_02
Patent number
US08114893B2

Reaction notes

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