Water → HCID 57460572, compound

HRID 1673996Notes

Reaction equation

HRID 1673996 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-0be9c4b1949f421c959ed873557d2b76
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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