HCID 178418361, compound → HCID 178481815, compound

HRID 2279493Notes

Reaction equation

HRID 2279493 reaction equation
C(OC([NH:11]/[C:12](=[N:20]\C(=O)OCC1C=CC=CC=1)/[NH:13][C:14]1[N:18]([CH3:19])[N:17]=[CH:16][CH:15]=1)=O)C1C=CC=CC=1.[H][H]>CCO.C1COCC1.[OH-].[OH-].[Pd+2]>[CH3:19][N:18]1[C:14]([NH:13][C:12]([NH2:20])=[NH:11])=[CH:15][CH:16]=[N:17]1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compound2×HCID 178481814HCID 178481814, compound

Product 1

HCID 178481815HCID 178481815, compoundYield 90.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a stirred solution of 180 (1.00 g, 2.45 mmol) in EtOH/THF (1:1, 35 mL) at RT was added Pearlman's Catalyst (0.172 g, 0.245 mmol). The mixture subjected to a vacuum/purge cycle three times with hydrogen gas and then maintained under 1 atmosphere balloon of hydrogen pressure. After stirring overnight and the reaction was filtered through GF/F filter paper with EtOH and the filtrate was concentrated to afford 0.31 g (90%) of 1-(1-methyl-1H-pyrazol-5-yl)guanidine (182) as a clear glass which was used without further purification: MS m/z (APCI-pos) M+1=140.0.

Workup

  1. filtrationthe reaction was filtered through GF/F
  2. filtrationfilter paper with EtOH
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-cafbd26a22314b1abc881d8e98721ecc
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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