Tetrabutylammonium Fluoride → 4'-{[4-(3-Hydroxy-2,2-dimethylpropyl)-2-methyl-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile

HRID 2048223Notes

Reaction equation

HRID 2048223 reaction equation
[Si]([O:8][CH2:9][C:10]([CH3:42])([CH3:41])[CH2:11][N:12]1[C:17](=[O:18])[C:16]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[C:27]([C:32]#[N:33])=[CH:28][CH:29]=[CH:30][CH:31]=3)=[CH:22][CH:21]=2)=[C:15]([CH2:34][CH2:35][CH3:36])[N:14]2[N:37]=[C:38]([CH3:40])[N:39]=[C:13]12)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:8][CH2:9][C:10]([CH3:41])([CH3:42])[CH2:11][N:12]1[C:17](=[O:18])[C:16]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]3[C:27]([C:32]#[N:33])=[CH:28][CH:29]=[CH:30][CH:31]=3)=[CH:24][CH:25]=2)=[C:15]([CH2:34][CH2:35][CH3:36])[N:14]2[N:37]=[C:38]([CH3:40])[N:39]=[C:13]12

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 670090144'-{[4-(3-{[Tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpropyl)-2-methyl-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile

Product 1

HCID 670087144'-{[4-(3-Hydroxy-2,2-dimethylpropyl)-2-methyl-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrileYield 81.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4′-{[4-(3-{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpropyl)-2-methyl-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile (1.5 g), tetrabutylammonium fluoride (1 M tetrahydrofuran solution, 4 mL) and tetrahydrofuran (30 mL) was stirred at room temperature for 3 hr. The reaction mixture was extracted with ethyl acetate and water, and the organic layer was washed with water and then 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 solid (0.98 g, 79%).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate and water
  2. washthe organic layer was washed with water
  3. dry with materialwith saturated brine, and dried 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-3e6358a67ebe48fea8743a3109124b3e
Source dataset
uspto-grants-2013_11
Patent number
US08592431B2

Reaction notes

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