Ammonium Chloride → 2-(5,7-Dichloropyrazolo[1,5-a]pyrimidin-6-yl)ethanol

HRID 1452616Notes

Reaction equation

HRID 1452616 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][CH:9]=[O:10])=[C:6]([Cl:11])[N:5]2[N:12]=[CH:13][CH:14]=[C:4]2[N:3]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO>[Cl:1][C:2]1[C:7]([CH2:8][CH2:9][OH:10])=[C:6]([Cl:11])[N:5]2[N:12]=[CH:13][CH:14]=[C:4]2[N:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 866137832-(5,7-Dichloropyrazolo[1,5-a]pyrimidin-6-yl)acetaldehyde

Product 1

HCID 575268292-(5,7-Dichloropyrazolo[1,5-a]pyrimidin-6-yl)ethanolYield 146.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The above aldehyde (1.82 mmol) was dissolved in methanol (27 mL), and sodium borohydride (302 mg, 7.98 mmol) was added to this solution with ice-cooling. After this mixture was stirred for 30 min, aqueous ammonium chloride was added here. The resultant mixture was extracted with ethyl acetate, and the organic layer was washed with brine and dried over sodium sulfate. After the sodium sulfate was filtered off, the solvent was distilled off, and the residue was purified with column chromatography (15% ethyl acetate-hexane) to obtain the title compound (617 mg).

Workup

  1. temperaturecooling
  2. extractionThe resultant mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter the sodium sulfate was filtered off
  6. distillationthe solvent was distilled off
  7. customthe residue was purified with column chromatography (15% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-d0ee2f71c925443fb96d97d43f472a63
Source dataset
uspto-grants-2009_01
Patent number
US07473694B2

Reaction notes

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