HCID 55285668, compound → HCID 67052527, compound
Reaction equation
O.[Na].[N+:3]([CH:6]([CH:9]=O)[CH:7]=O)([O-:5])=[O:4].[NH2:11][C:12]1[NH:16][N:15]=[C:14]([O:17][CH2:18][CH2:19][OH:20])[CH:13]=1>C(O)(=O)C.O>[N+:3]([C:6]1[CH:7]=[N:11][C:12]2[N:16]([N:15]=[C:14]([O:17][CH2:18][CH2:19][OH:20])[CH:13]=2)[CH:9]=1)([O-:5])=[O:4]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
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
- customThe cooled reaction mixture
- extractionthe mixture was extracted twice with DCM containing 25% IPA
- dry with materialThe organic extracts were dried over magnesium sulfate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-e0ba5ed5ddaf4e1aaa6cacb68abc87dc
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394795B2
Reaction notes
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