Hydrochloric Acid → HCID 68276036, compound

HRID 1475945Notes

Reaction equation

HRID 1475945 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:22]=[C:12]3[N:13]=[C:14]([C:17]([O:19]CC)=[O:18])[CH:15]=[CH:16][N:11]3[N:10]=2)=[CH:5][CH:4]=1.O.[OH-].[Li+].Cl>C1COCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:22]=[C:12]3[N:13]=[C:14]([C:17]([OH:19])=[O:18])[CH:15]=[CH:16][N:11]3[N:10]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 68276104HCID 68276104, compound

Product 1

HCID 68276036HCID 68276036, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidine-5-carboxylate (485 mg; 1.63 mmol) in THF (10 mL) and water (3 mL) was added lithium hydroxide hydrate (206 mg; 4.9 mmol) and the mixture was stirred at room temperature for 3 hours. Concentrated hydrochloric acid was then slowly added (ca. 0.5 mL) until pH reached 1 and the mixture was concentrated under reduced pressure. The resulting solid was dissolved in methylene chloride, filtered, concentrated and dried under high vacuum. The crude product was used directly in the next step. LCMS m/z 270.1 (M+H)+, ret. time=2.20 min.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. dissolutionThe resulting solid was dissolved in methylene chloride
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-521cb701fab446f19d89de04f6965684
Source dataset
uspto-grants-2015_04
Patent number
US09018395B2

Reaction notes

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