Tetrahydrofuran → HCID 178438855, compound

HRID 1688858Notes

Reaction equation

HRID 1688858 reaction equation
[O:1]=[C:2]1[C:7]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[C:17]([C:22]#[N:23])=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:12][CH:11]=2)[CH3:9])=[C:6]([CH2:24][CH2:25][CH3:26])[N:5]2[N:27]=[CH:28][N:29]=[C:4]2[N:3]1[CH:30]1[CH2:35][CH2:34][C:33](=[O:36])[CH2:32][CH2:31]1.O1CCCC1.[BH4-].[Na+]>CO>[OH:36][C@H:33]1[CH2:34][CH2:35][C@H:30]([N:3]2[C:2](=[O:1])[C:7]([CH:8]([C:10]3[CH:15]=[CH:14][C:13]([C:16]4[C:17]([C:22]#[N:23])=[CH:18][CH:19]=[CH:20][CH:21]=4)=[CH:12][CH:11]=3)[CH3:9])=[C:6]([CH2:24][CH2:25][CH3:26])[N:5]3[N:27]=[CH:28][N:29]=[C:4]23)[CH2:31][CH2:32]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 670104904'-{1-[5-Oxo-4-(4-oxocyclohexyl)-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]ethyl}biphenyl-2-carbonitrile

Product 1

HCID 178438855HCID 178438855, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 4′-{1-[5-oxo-4-(4-oxocyclohexyl)-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]ethyl}biphenyl-2-carbonitrile (1.38 g), tetrahydrofuran (15 mL) and methanol (10 mL) was added sodium borohydride (0.50 g) at 0° C., and the mixture was stirred at room temperature for 30 min. 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 oil (1.24 g, 89%).

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-698d3db429c541ada96c4595cbdd37de
Source dataset
uspto-grants-2012_04
Patent number
US08148383B2

Reaction notes

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