Hydrochloric Acid → 1-isopropyl-6-(4-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ol

HRID 1093184Notes

Reaction equation

HRID 1093184 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][N:6]([CH:20]([CH3:22])[CH3:21])[C:7]=1[NH:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)#[N:2].C([OH:25])C.OO.Cl>[OH-].[Na+]>[CH:20]([N:6]1[C:7]2=[N:8][C:9]([C:10]3[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=3)=[N:2][C:1]([OH:25])=[C:3]2[CH:4]=[N:5]1)([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 784Hydrogen PeroxideHCID 66589126N-(4-cyano-1-isopropyl-1H-pyrazol-5-yl)-4-nitrobenzamide

Product 1

HCID 1784566311-isopropyl-6-(4-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-olYield 58%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A suspension of N-(4-cyano-1-isopropyl-1H-pyrazol-5-yl)-4-nitrobenzamide (1.3 g, 4.3 mmol) in 1 M aqueous sodium hydroxide solution (9 mL) was made into a homogeneous mixture by the addition of approximately 40 mL of ethanol. Aqueous hydrogen peroxide solution (30%, 5 mL) was added and the mixture was slowly heated to reflux, at which state it remained overnight. After the mixture was allowed to cool to room temperature, it was treated with concentrated hydrochloric acid (5 mL), precipitating a light yellow solid. The solid was collected via Buchner filtration, washed with water, and dried under house vacuum to provide 1-isopropyl-6-(4-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ol as a pale yellow solid (0.76 g, 58%). MS (ES+): 299.8 (M+H)+

Workup

  1. temperaturethe mixture was slowly heated
  2. temperatureto reflux, at which state it
  3. customprecipitating a light yellow solid
  4. filtrationThe solid was collected via Buchner filtration
  5. washwashed with water
  6. customdried under house vacuum

Sources & evidence

ORD record
ord-b5e9f07e91884c2ba7481d66b1588695
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

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