Sodium Hydroxide → 3-(2-methylsulfanyl-pyrimidin-4-yl)-1-oxo-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole-2-carboxylic acid

HRID 1455251Notes

Reaction equation

HRID 1455251 reaction equation
C([O:3][C:4]([C:6]1[C:13](=[O:14])[N:9]2[CH2:10][CH2:11][CH2:12][N:8]2[C:7]=1[C:15]1[CH:20]=[CH:19][N:18]=[C:17]([S:21][CH3:22])[N:16]=1)=[O:5])C.[OH-].[Na+]>C1COCC1.C([O-])(O)=O.[Na+]>[CH3:22][S:21][C:17]1[N:16]=[C:15]([C:7]2[N:8]3[CH2:12][CH2:11][CH2:10][N:9]3[C:13](=[O:14])[C:6]=2[C:4]([OH:5])=[O:3])[CH:20]=[CH:19][N:18]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 574380853-(2-methylsulfanyl-pyrimidin-4-yl)-1-oxo-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole-2-carboxylic acid ethyl ester

Product 1

HCID 574380863-(2-methylsulfanyl-pyrimidin-4-yl)-1-oxo-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 3-(2-methylsulfanyl-pyrimidin-4-yl)-1-oxo-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole-2-carboxylic acid ethyl ester, 13, (2.7 g, 8.4 mmol) in THF (85 mL) is added aqueous NaOH (42 mL of 1N solution, 42.0 mmol). The solution is stirred for 18 hours at room temperature then diluted with aqueous saturated NaHCO3 and the aqueous phase is extracted twice with CHCl3. The aqueous phase is then acidified to pH 1 with aqueous 1N HCl and extracted twice with CHCl3. The combined organic layers are dried (MgSO4), filtered and concentrated in vacuo to afford 2.3 g of the desired product which is used without further purification.

Workup

  1. extractionthe aqueous phase is extracted twice with CHCl3
  2. extractionextracted twice with CHCl3
  3. dry with materialThe combined organic layers are dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ef01f40360f64a23950f134d93023686
Source dataset
uspto-grants-2009_01
Patent number
US07482356B2

Reaction notes

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