Ammonia → 3-(4,5,6,7-Tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)propionamide

HRID 349566Notes

Reaction equation

HRID 349566 reaction equation
[N:1]1[N:5]2[CH2:6][CH2:7][CH2:8][NH:9][C:4]2=[C:3]([CH2:10][CH2:11][C:12]([O:14]CC)=O)[CH:2]=1.[NH3:17]>>[N:1]1[N:5]2[CH2:6][CH2:7][CH2:8][NH:9][C:4]2=[C:3]([CH2:10][CH2:11][C:12]([NH2:17])=[O:14])[CH:2]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 135732757Ethyl 3-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)propionate

Product 1

HCID 1357327583-(4,5,6,7-Tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)propionamide

Procedure

A solution of ethyl 3-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)propionate (30 g) in saturated methanolic ammonia solution (700 ml) was stirred at 110° C. for 5 days in an autoclave. After evaporation of the solvent in vacuo, methylene chloride was added to the residue. The resulting solid was collected by filtration and dissolved in methanol. To the solution was added activated charcoal, and the mixture was filtered. The filtrate was concentrated in vacuo. The residue was triturated with acetonitrile and dried in vacuo to give 3-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)propionamide (11.3 g) as a solid.

Workup

  1. customAfter evaporation of the solvent in vacuo, methylene chloride
  2. additionwas added to the residue
  3. filtrationThe resulting solid was collected by filtration
  4. dissolutiondissolved in methanol
  5. additionTo the solution was added
  6. filtrationthe mixture was filtered
  7. concentrationThe filtrate was concentrated in vacuo
  8. customThe residue was triturated with acetonitrile
  9. customdried in vacuo

Sources & evidence

ORD record
ord-06e00ee6780b452fb391910a4328ba63
Source dataset
uspto-grants-2007_02
Patent number
US07179801B2

Reaction notes

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