4'-{[6-ethyl-3-(1-methyl-2-oxoethyl)-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile → 4'-{[6-ethyl-3-[2-hydroxy-2-(4-methoxyphenyl)-1-methylethyl]-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile

HRID 1889367Notes

Reaction equation

HRID 1889367 reaction equation
[CH2:1]([C:3]1[S:32][C:6]2[N:7]([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][CH:19]=3)[C:8](=[O:16])[N:9]([CH:12]([CH3:15])[CH:13]=[O:14])[C:10](=[O:11])[C:5]=2[CH:4]=1)[CH3:2].[CH3:33][O:34][C:35]1[CH:40]=[CH:39][C:38]([Mg]Br)=[CH:37][CH:36]=1>O1CCCC1>[CH2:1]([C:3]1[S:32][C:6]2[N:7]([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][CH:19]=3)[C:8](=[O:16])[N:9]([CH:12]([CH3:15])[CH:13]([OH:14])[C:38]3[CH:39]=[CH:40][C:35]([O:34][CH3:33])=[CH:36][CH:37]=3)[C:10](=[O:11])[C:5]=2[CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 593515604'-{[6-ethyl-3-(1-methyl-2-oxoethyl)-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrileHCID 178491912HCID 178491912, compound

Product 1

HCID 593517204'-{[6-ethyl-3-[2-hydroxy-2-(4-methoxyphenyl)-1-methylethyl]-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrileYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 4′-{[6-ethyl-3-(1-methyl-2-oxoethyl)-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile (1.7 g) and tetrahydrofuran (100 mL) was added 4-methoxyphenyl-magnesium bromide (12.6 mL), and the mixture was stirred at 50° C. for 16 hr. The reaction mixture was extracted with saturated aqueous ammonium chloride solution and ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as a colorless amorphous solid (0.68 g, 32%).

Workup

  1. extractionThe reaction mixture was extracted with saturated aqueous ammonium chloride solution and ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ff04d279ee54488b85529d9e3d3d4700
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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