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Ethyl Acetate → 3-Cyano-6-hydroxy-7-oxo-1,7-dihydro-pyrazolo[1,5-a]pyrimidine-5-carboxylic acid methyl ester

HRID 536116
Notes
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Reaction equation

HRID 536116 reaction equation
[NH2:1][C:2]1[C:6]([C:7]#[N:8])=[CH:5][NH:4][N:3]=1.O/[C:10](/[C:16]([O-:18])=[O:17])=[C:11](/[OH:15])\[C:12]([O-:14])=O.[C:19](OCC)(=O)C>C(O)(=O)C>[CH3:19][O:18][C:16]([C:10]1[N:1]=[C:2]2[C:6]([C:7]#[N:8])=[CH:5][NH:4][N:3]2[C:12](=[O:14])[C:11]=1[OH:15])=[O:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 178510443HCID 178510443, compoundHCID 178526009HCID 178526009, compound

Product 1

HCID 574945263-Cyano-6-hydroxy-7-oxo-1,7-dihydro-pyrazolo[1,5-a]pyrimidine-5-carboxylic acid methyl esterYield 62%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

3-amino-4-pyrazole carbonitrile (400 mg, 3.7 mmol) and dihydroxyfumarate (978 mg, 5.5 mmol) were dissolved in glacial acetic acid (5 mL) and the mixture was heated to 100° C. After 2 d, the reaction was complete by HPLC analysis and was cooled to room temperature. Ethyl acetate (10 mL) was added to initiate precipitation of product and the resulting precipitate was collected by filtration. The product was isolated in 62% yield (534 mg).

Workup

  1. temperaturewas cooled to room temperature
  2. customprecipitation of product
  3. filtrationthe resulting precipitate was collected by filtration
  4. customThe product was isolated in 62% yield (534 mg)

Sources & evidence

ORD record
ord-f3ff9463ae3846449a31a3747e8f3947
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08859563B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes