Ethyl 3-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)acrylate → Ethyl 3-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)propionate

HRID 349561Notes

Reaction equation

HRID 349561 reaction equation
[N:1]1[N:5]2[CH2:6][CH2:7][CH2:8][NH:9][C:4]2=[C:3]([CH:10]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:2]=1>C(O)C.O1CCCC1.[C].[Pd]>[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][CH2:15][CH3:16])=[O:13])[CH:2]=1

Participants

5

Reactant 1

HCID 136334104Ethyl 3-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)acrylate

Product 1

HCID 135732757Ethyl 3-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)propionateYield 110.1%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 3-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)acrylate (45 g) in a mixture of ethanol (800 ml) and tetrahydrofuran (400 ml) was treated with 10% palladium carbon (2.2 g) under a hydrogen atmosphere at room temperature for 22 hours. After the catalyst was filtered off, the filtrate was concentrated in vacuo to give ethyl 3-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)propionate (50 g) as an oil.

Workup

  1. filtrationAfter the catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8761ec88a9d0455cb3519617939bb9b2
Source dataset
uspto-grants-2007_02
Patent number
US07179801B2

Reaction notes

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