Sodium borohydride → 5-[3-(1-hydroxyethyl)benzyl]-6-methyl-3-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-2-propylpyrimidin-4(3H)-one

HRID 1718280Notes

Reaction equation

HRID 1718280 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:38]=[CH:39][CH:40]=1)[CH2:7][C:8]1[C:9](=[O:37])[N:10]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[NH:35][C:34](=[O:36])[O:33][N:32]=3)=[CH:21][CH:20]=2)[C:11]([CH2:15][CH2:16][CH3:17])=[N:12][C:13]=1[CH3:14])(=[O:3])[CH3:2].[BH4-].[Na+]>O1CCCC1CO.C(OCC)(=O)C>[OH:3][CH:1]([C:4]1[CH:5]=[C:6]([CH:38]=[CH:39][CH:40]=1)[CH2:7][C:8]1[C:9](=[O:37])[N:10]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[NH:35][C:34](=[O:36])[O:33][N:32]=3)=[CH:21][CH:20]=2)[C:11]([CH2:15][CH2:16][CH3:17])=[N:12][C:13]=1[CH3:14])[CH3:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 1360267495-(3-acetylbenzyl)-6-methyl-3-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-2-propylpyrimidin-4(3H)-one

Product 1

HCID 1360267505-[3-(1-hydroxyethyl)benzyl]-6-methyl-3-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-2-propylpyrimidin-4(3H)-oneYield 69.7%

Reagents, catalysts & solvents 2

HCID 7360Tetrahydrofurfuryl alcoholSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(3-acetylbenzyl)-6-methyl-3-{[2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-2-propylpyrimidin-4(3H)-one (0.20 g) in tetrahydrofuran-methanol (1:1, 4 mL) was added sodium borohydride (0.014 g), and the mixture was stirred for 30 min. The reaction mixture was diluted with ethyl acetate, washed with 1 M hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (0.14 g, 69%) as a colorless solid.

Workup

  1. washwashed with 1 M hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f0a1d2446acf4df1b5458601b8362f15
Source dataset
uspto-grants-2010_09
Patent number
US07803940B2

Reaction notes

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