Ammonium Chloride → HCID 57752947, compound

HRID 225996Notes

Reaction equation

HRID 225996 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([Cl:9])[N:5]2[N:10]=[CH:11][C:12]([CH:13]=[O:14])=[C:4]2[N:3]=1.[BH4-].[Na+].[NH4+].[Cl-]>C(O)C>[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([Cl:9])[N:5]2[N:10]=[CH:11][C:12]([CH2:13][OH:14])=[C:4]2[N:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 57752942HCID 57752942, compound

Product 1

HCID 57752947HCID 57752947, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 5,7-dichloro-6-methylpyrazolo[1,5-a]pyrimidine-3-carbaldehyde (200 mg) in ethanol (20 mL) was added sodium borohydride (70 mg) and the reaction mixture was stirred at room temperature for 15 min. Saturated aqueous NH4Cl (1 mL) was added and the reaction mixture was stirred for a further 10 min then the solvent was removed under reduced pressure. Water and ethyl acetate were added and the product was extracted with ethyl acetate (3×). The combined organic phase was washed (water, saturated aqueous NaCl) and dried (MgSO4) to give the title compound (150 mg); 1H-NMR (400 MHz, CDCl3) d(ppm): 8.22 (1H, s, 2-H), 4.90 (1H, s, CH2OH).

Workup

  1. stirringthe reaction mixture was stirred for a further 10 min
  2. customthe solvent was removed under reduced pressure
  3. additionWater and ethyl acetate were added
  4. extractionthe product was extracted with ethyl acetate (3×)
  5. washThe combined organic phase was washed (water, saturated aqueous NaCl)
  6. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-c1dc3376b3884796aa338a3966a1423a
Source dataset
uspto-grants-2009_07
Patent number
US07557110B2

Reaction notes

Loading…