Water → 2-(Hydroxymethyl)pyrazolo[1,5-A]pyrimidine-6-carboxylic acid

HRID 1393663Notes

Reaction equation

HRID 1393663 reaction equation
[OH-].[Na+].[OH:3][CH2:4][C:5]1[CH:18]=[C:8]2[N:9]=[CH:10][C:11]([C:13]([O:15]CC)=[O:14])=[CH:12][N:7]2[N:6]=1.O>O1CCCC1>[OH:3][CH2:4][C:5]1[CH:18]=[C:8]2[N:9]=[CH:10][C:11]([C:13]([OH:15])=[O:14])=[CH:12][N:7]2[N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 23091920Ethyl 2-(hydroxymethyl)pyrazolo[1,5-A]pyrimidine-6-carboxylate

Product 1

HCID 230919552-(Hydroxymethyl)pyrazolo[1,5-A]pyrimidine-6-carboxylic acidYield 66.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5 N Sodium hydroxide solution (0.1 ml) was added to a solution of the thus obtained ethyl 2-hydroxymethylpyrazolo[1,5-a]pyrimidine-6-carboxylate (19 mg) in tetrahydrofuran (1 ml), and stirred for 17 hours at room temperature. After water was added, the reaction mixture was washed with ethyl acetate. The aqueous phase was acidified by 2 N hydrochloric acid, extracted with ethyl acetate and dried over sodium sulfate anhydrous. The resulting product was concentrated under reduced pressure, and the residue was dissolved in hot ethyl acetate and then filtered. The filtrate was concentrated under reduced pressure to give the title compound (11 mg, Y.:65%).

Workup

  1. washthe reaction mixture was washed with ethyl acetate
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate anhydrous
  4. concentrationThe resulting product was concentrated under reduced pressure
  5. dissolutionthe residue was dissolved in hot ethyl acetate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-29a953d2324e4c91879369d745b8d1ef
Source dataset
uspto-grants-2008_03
Patent number
US07345180B2

Reaction notes

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