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

HRID 1518282Notes

Reaction equation

HRID 1518282 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

To a solution of compound 21C (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 under reduced pressure and the concentrate was dissolved in 8 mL of water. The aqueous solution was acidified with diluted HCl. A white precipitate was collected, washed with water, and dried to provide the desired product 21D: 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. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe concentrate was dissolved in 8 mL of water
  3. customA white precipitate was collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-54b4b1456d9644c8af7d5c4f4a9a6465
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

Loading…