Sodium borohydride → HCID 136063907, compound

HRID 1412663Notes

Reaction equation

HRID 1412663 reaction equation
[OH:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:15](=[O:16])[C:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]4[NH:34][C:33](=[O:35])[O:32][N:31]=4)=[CH:20][CH:19]=3)=[C:13]([CH2:36][CH2:37][CH3:38])[N:12]3[N:39]=[CH:40][N:41]=[C:11]23)=[CH:6][CH:5]=1)[CH3:3].[BH4-].[Na+]>CO>[C:2]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:15](=[O:16])[C:14]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]4[NH:34][C:33](=[O:35])[O:32][N:31]=4)=[CH:22][CH:23]=3)=[C:13]([CH2:36][CH2:37][CH3:38])[N:12]3[N:39]=[CH:40][N:41]=[C:11]23)=[CH:6][CH:5]=1)(=[O:1])[CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 136063899HCID 136063899, compound

Product 1

HCID 136063907HCID 136063907, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution (10 mL) of 4-[4-(1-hydroxyethyl)phenyl]-6-{[2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-7-propyl[1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-one (0.05 g) in methanol was added sodium borohydride (0.039 g), and the mixture was stirred at room temperature for 1 hr. After evaporation of the solvent under reduced pressure, the residue was extracted with water and ethyl acetate. The obtained ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.036 g, 72%).

Workup

  1. customAfter evaporation of the solvent under reduced pressure
  2. extractionthe residue was extracted with water and ethyl acetate
  3. washThe obtained ethyl acetate layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cdf6ad54e8454705b436714901f27426
Source dataset
uspto-grants-2014_12
Patent number
US08921379B2

Reaction notes

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