Tetrabutylammonium Fluoride → 3-(4-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)-2-methyl-5-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-6-propylpyrimidin-4(3H)-one

HRID 1718524

Reaktionsgleichung

Reaktionsgleichung von HRID 1718524
[CH3:1][C:2]1([CH3:53])[CH2:11][CH:10]([O:12][Si](C(C)C)(C(C)C)C(C)C)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N:23]3[C:28](=[O:29])[C:27]([CH2:30][C:31]4[CH:36]=[CH:35][C:34]([C:37]5[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=5[C:43]5[NH:47][C:46](=[O:48])[O:45][N:44]=5)=[CH:33][CH:32]=4)=[C:26]([CH2:49][CH2:50][CH3:51])[N:25]=[C:24]3[CH3:52])[CH:8]=2)[O:3]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[OH:12][CH:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N:23]3[C:28](=[O:29])[C:27]([CH2:30][C:31]4[CH:32]=[CH:33][C:34]([C:37]5[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=5[C:43]5[NH:47][C:46](=[O:48])[O:45][N:44]=5)=[CH:35][CH:36]=4)=[C:26]([CH2:49][CH2:50][CH3:51])[N:25]=[C:24]3[CH3:52])[CH:8]=2)[O:3][C:2]([CH3:1])([CH3:53])[CH2:11]1

Komponenten

5

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 1361467753-{2,2-dimethyl-4-[(triisopropylsilyl)oxy]-3,4-dihydro-2H-chromen-6-yl}-2-methyl-5-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-6-propylpyrimidin-4(3H)-one

Produkt 1

HCID 1359558823-(4-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)-2-methyl-5-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-6-propylpyrimidin-4(3H)-oneAusbeute 95,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3-{2,2-dimethyl-4-[(triisopropylsilyl)oxy]-3,4-dihydro-2H-chromen-6-yl}-2-methyl-5-{[2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-6-propylpyrimidin-4(3H)-one (4.0 g) in tetrahydrofuran (20 mL) was added tetrabutylammonium fluoride (1.0 M tetrahydrofuran solution, 8.2 mL), and the mixture was stirred for 2 hr. The reaction mixture was diluted with ethyl acetate, washed with 5% aqueous potassium hydrogen sulfate solution and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give the title compound (3.0 g, 95%) as a solid.

Aufarbeitung

  1. washwashed with 5% aqueous potassium hydrogen sulfate solution
  2. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fc704b93bbf445c8b218bdb357daa186
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803940B2

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