Sodium borohydride → (6-Methyl-2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)methanol

HRID 1896422Notes

Reaction equation

HRID 1896422 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:10]=2[CH:11]=[O:12])[CH:7]=1.[BH4-].[Na+]>CO>[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:10]=2[CH2:11][OH:12])[CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 577430426-Methyl-2-phenylpyrazolo[1,5-a]pyrimidine-3-carbaldehyde

Product 1

HCID 57743005(6-Methyl-2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)methanolYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-methyl-2-phenylpyrazolo[1,5-a]pyrimidine-3-carbaldehyde x26 (3.37 mmol, 1 eq, 0.8 g) in MeOH (20 ml) maintained at 0° C. is added sodium borohydride (3.7 mmol, 1.1 eq, 0.14 g) and the resulting solution is stirred at room temperature during 0.5 hour. After this time, the solvent is removed under reduced pressure. The solid residue is washed with water, filtered and dried (under vacuum) to give 0.58 g of pure (6-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)methanol x143.

Workup

  1. customAfter this time, the solvent is removed under reduced pressure
  2. washThe solid residue is washed with water
  3. filtrationfiltered
  4. customdried (under vacuum)

Sources & evidence

ORD record
ord-bd0cab24dfd64470b725e77b8820e2b4
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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