Dimethylformamide → 4'-{[3-(4-{[tert-butyl(dimethyl)silyl]oxy}-2-hydroxy-3,3-dimethylbutyl)-6-ethyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile

HRID 1889393Notes

Reaction equation

HRID 1889393 reaction equation
[CH2:1]([C:3]1[S:28][C:6]2[N:7]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:16][CH:15]=3)[C:8](=[O:12])[NH:9][C:10](=[O:11])[C:5]=2[CH:4]=1)[CH3:2].[C:29]([Si:33]([CH3:43])([CH3:42])[O:34][CH2:35][C:36]([CH3:41])([CH:38]1[CH2:40][O:39]1)[CH3:37])([CH3:32])([CH3:31])[CH3:30].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O.C(OCC)(=O)C>[Si:33]([O:34][CH2:35][C:36]([CH3:37])([CH3:41])[CH:38]([OH:39])[CH2:40][N:9]1[C:10](=[O:11])[C:5]2[CH:4]=[C:3]([CH2:1][CH3:2])[S:28][C:6]=2[N:7]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:16][CH:15]=2)[C:8]1=[O:12])([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:43])[CH3:42]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 593517704'-[(6-ethyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl)methyl]biphenyl-2-carbonitrileHCID 86642154Tert-butyl(dimethyl) (2-methyl-2-oxirane-2-ylpropoxy)silane

Product 1

HCID 593515284'-{[3-(4-{[tert-butyl(dimethyl)silyl]oxy}-2-hydroxy-3,3-dimethylbutyl)-6-ethyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrileYield 43%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4′-[(6-ethyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl)methyl]biphenyl-2-carbonitrile (2.0 g), tert-butyl(dimethyl) (2-methyl-2-oxirane-2-ylpropoxy)silane (3.75 g), potassium carbonate (1.38 g) and N,N-dimethylformamide (15 mL) was stirred at 80° C. for 24 hr. After allowing to cool to room temperature, ethyl acetate and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was successively washed with water and 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 pale-yellow amorphous solid (1.36 g, 43%).

Workup

  1. temperatureto cool to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was successively washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-16a62942e4364bbe90bcea7b8aa67e6c
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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