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Hydrochloric Acid → Ethyl 7-amino-mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-carboxylate

HRID 965998
Notes
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Reaction equation

HRID 965998 reaction equation
Cl.[C:2]1([CH3:17])[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[C:10]1[C:11]([CH3:16])=[N:12][NH:13][C:14]=1[NH2:15].[C:18]([C:20](=[C:26](OCC)[CH3:27])[C:21]([O:23][CH2:24][CH3:25])=[O:22])#[N:19]>CO>[NH2:19][C:18]1[N:13]2[N:12]=[C:11]([CH3:16])[C:10]([C:3]3[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=3[CH3:17])=[C:14]2[N:15]=[C:26]([CH3:27])[C:20]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 46635Ethyl 2-cyano-3-ethoxy-2-butenoateHCID 178424562HCID 178424562, compound

Product 1

HCID 22249773Ethyl 7-amino-mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-carboxylateYield 20.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Concentrated hydrochloric acid (0.1 mL) was added to a solution of 4-mesityl-3-methyl-1H-5-pyrazoleamine (2.5 g, 11.61 mmol) and ethyl 2-cyano-3-ethoxy-2-butenoate (2.13 g, 11.61 mmol) in methanol (30 mL), followed by heating under reflux for 18 hours. The reaction mixture was evaporated as it was. Then, water was added and a 5N aqueous solution of sodium hydroxide was added under ice-cooling, to neutralize. Further, the mixture was extracted with ethyl acetate, and the organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (15% ethyl acetate/hexane), to give the title compound (835 mg).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 18 hours
  3. customThe reaction mixture was evaporated as it
  4. additionThen, water was added
  5. additiona 5N aqueous solution of sodium hydroxide was added under ice-
  6. temperaturecooling
  7. extractionFurther, the mixture was extracted with ethyl acetate
  8. washthe organic layer was washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customevaporated
  11. customThe residue was purified by silica gel column chromatography (15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-af8f0395d22b46a497e7bff9652ebe72
Source dataset
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06951865B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes