Sodium borohydride → HCID 59351709, compound

HRID 1889332Notes

Reaction equation

HRID 1889332 reaction equation
[CH2:1]([C:3]1[S:37][C:6]2[N:7]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]4[C:30]([C:35]#[N:36])=[CH:31][CH:32]=[CH:33][CH:34]=4)=[CH:25][CH:24]=3)[C:8](=[O:21])[N:9]([CH2:12][CH2:13][N:14]3[CH:18]=[CH:17][N:16]=[C:15]3[CH:19]=[O:20])[C:10](=[O:11])[C:5]=2[CH:4]=1)[CH3:2].[BH4-].[Na+]>CO>[CH2:1]([C:3]1[S:37][C:6]2[N:7]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]4[C:30]([C:35]#[N:36])=[CH:31][CH:32]=[CH:33][CH:34]=4)=[CH:25][CH:24]=3)[C:8](=[O:21])[N:9]([CH2:12][CH2:13][N:14]3[CH:18]=[CH:17][N:16]=[C:15]3[CH2:19][OH:20])[C:10](=[O:11])[C:5]=2[CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59351610HCID 59351610, compound

Product 1

HCID 59351709HCID 59351709, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution (40 mL) of 4′-{[6-ethyl-3-[2-(2-formyl-1H-imidazol-1-yl)ethyl]-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile (2.2 g) in methanol was added sodium borohydride (0.27 g), and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated under reduced pressure, and 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. The residue was purified by silica gel column chromatography to give the title compound as colorless crystals (2.0 g, 91%).

Workup

  1. customThe solvent was evaporated 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-6f81d42b03f1475cac1ea2f67de59575
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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