Sodium Hydroxide → 1,6-Bis(1,1-dimethylethyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

HRID 1522491Notes

Reaction equation

HRID 1522491 reaction equation
[CH3:1][C:2]([N:5]1[C:9]2[N:10]=[C:11]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:12]=[C:13]([C:14]([O:16]CC)=[O:15])[C:8]=2[C:7]([CH3:23])=[N:6]1)([CH3:4])[CH3:3].[OH-].[Na+]>CCO>[CH3:4][C:2]([N:5]1[C:9]2[N:10]=[C:11]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:12]=[C:13]([C:14]([OH:16])=[O:15])[C:8]=2[C:7]([CH3:23])=[N:6]1)([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68081092Ethyl 1,6-bis(1,1-dimethylethyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Product 1

HCID 680786001,6-Bis(1,1-dimethylethyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an EtOH solution (8 mL) of ethyl 1,6-bis(1,1-dimethylethyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (528 mg, 1.663 mmol) was added sodium hydroxide (2.77 mL, 8.32 mmol), and the mixture was stirred for at room temperature for 2 h. The volatiles were removed under reduced pressure and the aqueous phase was acidified using 1H HCl to ˜pH 3. The precipitate was filtered, washed with water, and dried under high vacuum to give the product as 445 mg (92%). LCMS E-S (M+H)=289.4. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.49 (s, 9 H), 1.76 (s, 9 H), 2.51 (s, 3 H), 7.51 (s, 1 H).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried under high vacuum
  5. customto give the product as 445 mg (92%)

Sources & evidence

ORD record
ord-967e62ba895640bfa4b7fb0ba53aa374
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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