Tributylphosphine → 4'-[(1-{[5-({[Tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-yl]methyl}-2-methyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile

HRID 1674149Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1674149
[CH3:1][C:2]1[NH:3][C:4](=[O:26])[C:5]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19]([C:24]#[N:25])=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:14][CH:13]=2)=[C:6]([CH2:8][CH2:9][CH3:10])[N:7]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC.[Si:58]([O:65][CH2:66][C:67]1[CH:68]=[CH:69][C:70]([CH2:73]O)=[N:71][CH:72]=1)([C:61]([CH3:64])([CH3:63])[CH3:62])([CH3:60])[CH3:59]>O1CCCC1>[Si:58]([O:65][CH2:66][C:67]1[CH:68]=[CH:69][C:70]([CH2:73][N:3]2[C:4](=[O:26])[C:5]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([C:18]4[C:19]([C:24]#[N:25])=[CH:20][CH:21]=[CH:22][CH:23]=4)=[CH:14][CH:13]=3)=[C:6]([CH2:8][CH2:9][CH3:10])[N:7]=[C:2]2[CH3:1])=[N:71][CH:72]=1)([C:61]([CH3:64])([CH3:63])[CH3:62])([CH3:59])[CH3:60]

Komponenten

6

Edukt 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 224732225-(tert-Butyldimethylsilyloxymethyl)-2-(hydroxymethyl)pyridineHCID 1354272734'-[(2-Methyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile

Produkt 1

HCID 574607604'-[(1-{[5-({[Tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-yl]methyl}-2-methyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrileAusbeute 53,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 4′-[(2-methyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile (0.6 g), 1,1′-(azodicarbonyl)dipiperidine (0.48 g), tributylphosphine (0.95 g), [5-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-yl]methanol (0.48 g) and tetrahydrofuran (50 mL) was stirred at room temperature for 4 hr. The reaction mixture was concentrated, and the residue was diluted with ethyl acetate, washed with water 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 as a colorless solid (0.54 g, 49%).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with water
  4. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d397b2b55e7b4801b5194042d32f4627
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07998968B2

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