Hydrochloric Acid → HCID 178467745, compound

HRID 1602875Notes

Reaction equation

HRID 1602875 reaction equation
[OH:1][C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([CH2:11][CH2:12][C:13](=[O:15])[CH3:14])[CH:3]=1.[BH4-].[Na+].Cl>CO>[OH:1][C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([CH2:11][CH2:12][CH:13]([OH:15])[CH3:14])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 178467744HCID 178467744, compound

Product 1

HCID 178467745HCID 178467745, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

The compound obtained in step (2), 5.7 g, was dissolved in 120 ml of methanol. Sodium borohydride, 0.53 g, was added to the solution under ice-cooling. The mixture was stirred at 0° C. for 2 hours. After completion of the reaction, the reaction mixture was acidified by adding diluted hydrochloric acid dropwise and then extracted with chloroform. The organic layer was collected, washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was recrystallized from ethanol-n-hexane to provide 4.16 g of 7-hydroxy-5-(3-hydroxybutyl)pyrazolo[1,5-a]pyrimidine as colorless crystals.

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. extractionextracted with chloroform
  4. customThe organic layer was collected
  5. washwashed with saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was recrystallized from ethanol-n-hexane

Sources & evidence

ORD record
ord-d446fcda362c43178b35e999d79fcfcc
Source dataset
uspto-grants-1999_11
Patent number
US05985882

Reaction notes

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