Hydrochloric Acid → HCID 178467745, compound

HRID 1456000Notes

Reaction equation

HRID 1456000 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, compoundYield 72.3%

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 thereto while being ice-cooled. 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 a saturated 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. temperaturecooled
  2. customAfter completion of the reaction
  3. extractionextracted with chloroform
  4. customThe organic layer was collected
  5. washwashed with a saturated 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-0b4adc4a80fb4ccb873dd94f953d9bbc
Source dataset
uspto-grants-1998_12
Patent number
US05843951

Reaction notes

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