Water → HCID 57460572, compound

HRID 1718666Notes

Reaction equation

HRID 1718666 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:15](=[O:16])[C:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[C:25]([C:30]#[N:31])=[CH:26][CH:27]=[CH:28][CH:29]=4)=[CH:20][C:19]=3[F:32])=[C:13]([CH2:33][CH2:34][CH2:35][CH3:36])[N:12]=[C:11]2[CH3:37])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].C(OCC)(=O)C.O>C(O)C>[CH2:33]([C:13]1[N:12]=[C:11]([CH3:37])[N:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([CH:1]([OH:3])[CH3:2])[CH:5]=2)[C:15](=[O:16])[C:14]=1[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:25]([C:30]#[N:31])=[CH:26][CH:27]=[CH:28][CH:29]=2)=[CH:20][C:19]=1[F:32])[CH2:34][CH2:35][CH3:36]

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 57460571HCID 57460571, compound

Product 1

HCID 57460572HCID 57460572, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4′-{[1-(3-acetylphenyl)-4-butyl-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl]methyl}-3′-fluorobiphenyl-2-carbonitrile (1.17 g) in ethanol (10 mL) was added sodium tetrahydroboron (0.11 g), and the mixture was stirred for 3 hr. Ethyl acetate and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography to give the title compound as a pale-yellow viscous substance (0.97 g, 82%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e017c4c96e7848c0aff9a77bd6847db8
Source dataset
uspto-grants-2010_09
Patent number
US07803940B2

Reaction notes

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