Sodium Bicarbonate → HCID 67053911, compound

HRID 1943956Notes

Reaction equation

HRID 1943956 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[N:8]([N:10]=[C:11]([O:13][CH2:14][CH2:15][OH:16])[CH:12]=2)[CH:9]=1)([O-:3])=[O:2].C(=O)(O)[O-].[Na+]>O>[N+:1]([C:4]1[CH:9]=[C:12]2[C:11]([O:13][CH2:14][CH2:15][OH:16])=[N:10][NH:8][C:7]2=[N:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 67052527HCID 67052527, compound

Product 1

HCID 67053911HCID 67053911, compoundYield 9.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Nitromalonaldehyde sodium salt monohydrate (1.46 g, 9.29 mmol) was added to crude 2-(5-amino-1H-pyrazol-3-yloxy)ethanol (3.28 g) with salts (1.33 g, 9.29 mmol theoretical) in acetic acid (10 mL). This was heated at 90° C. for 2 hours. The cooled reaction mixture was diluted with water, and the mixture was extracted twice with DCM containing 25% IPA. The organic extracts were dried over magnesium sulfate, filtered, and evaporated to yield regioisomer 2-(6-nitropyrazolo[1,5-a]pyrimidin-2-yloxy)ethanol (0.77 g, 3.43 mmol) as a solid. The 2-(6-nitropyrazolo[1,5-a]pyrimidin-2-yloxy)ethanol (460 mg, 2.9 mmol) was suspended in water (40 mL), treated with saturated aqueous sodium bicarbonate (2 mL), and the mixture was refluxed for 2 hours. The cooled reaction mixture was extracted three times with DCM containing 25% IPA. The organic extracts were dried over magnesium sulfate, filtered, and evaporated to an oil. The crude material was purified by column chromatography with ethyl acetate to provide 2-(5-nitro-1H-pyrazolo[3,4-b]pyridin-3-yloxy)ethanol (60 mg, 0.27 mmol, 2.9% yield) as a solid.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. customThe cooled reaction mixture
  3. extractionwas extracted three times with DCM containing 25% IPA
  4. dry with materialThe organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to an oil
  7. customThe crude material was purified by column chromatography with ethyl acetate

Sources & evidence

ORD record
ord-a0579d3e50224d089171fc97b4db8a30
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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