Citric Acid → HCID 66847900, compound

HRID 1631300Notes

Reaction equation

HRID 1631300 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]2[CH:18]=[CH:17][N:16]3[N:19]=[CH:20][C:21]([C:22]([O:24]CC)=[O:23])=[C:15]3[N:14]=2)[CH:5]=[N:6][CH:7]=1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[Na+].[Cl-]>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]2[CH:18]=[CH:17][N:16]3[N:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[C:15]3[N:14]=2)[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 66853421HCID 66853421, compound

Product 1

HCID 66847900HCID 66847900, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 5-(2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (0.540 g, 1.52 mmol) was dissolved in MeOH (20 mL) and treated with 1N NaOH (13 mL). After stirring for 5 days, citric acid (solid) was added to acidify the mixture to pH 4-5. Saturated aqueous NaCl (10 mL) was added and the reaction mixture extracted with DCM and EtOAc. The combined organic layers were combined to afford 5-(2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (0.49 g, 99% yield). MS (apci) m/z=328.0 (M+H).

Workup

  1. extractionthe reaction mixture extracted with DCM and EtOAc

Sources & evidence

ORD record
ord-8f321eddff2641408964490557d2144b
Source dataset
uspto-grants-2014_07
Patent number
US08791123B2

Reaction notes

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