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2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → tert-Butyl 5-(benzyloxy)-2-{(1-[4'-({[tert-butyl(dimethyl)silyl]oxy}methyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidine-4-carboxylate

HRID 1626780
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Reaktionsgleichung

Reaktionsgleichung von HRID 1626780
Cl.[CH2:2]([O:9][C:10]1[C:11]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[N:12][C:13]([CH2:17][CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[N:14][C:15]=1[CH3:16])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[C:32]1[CH:37]=[CH:36][C:35]([C:38]2[CH:43]=[CH:42][C:41]([CH2:44][O:45][Si:46]([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:48])[CH3:47])=[CH:40][CH:39]=2)=[CH:34][CH:33]=1.CC(C)([O-])C.[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:2]([O:9][C:10]1[C:11]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[N:12][C:13]([CH2:17][CH:18]2[CH2:23][CH2:22][N:21]([C:32]3[CH:33]=[CH:34][C:35]([C:38]4[CH:43]=[CH:42][C:41]([CH2:44][O:45][Si:46]([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:47])[CH3:48])=[CH:40][CH:39]=4)=[CH:36][CH:37]=3)[CH2:20][CH2:19]2)=[N:14][C:15]=1[CH3:16])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 67156013tert-Butyl 5-(benzyloxy)-6-methyl-2-(piperidin-4-ylmethyl)pyrimidine-4-carboxylate hydrochlorideHCID 68193270[(4'-Bromobiphenyl-4-yl)methoxy](tert-butyl)dimethylsilane

Produkt 1

HCID 68193315
tert-Butyl 5-(benzyloxy)-2-{(1-[4'-({[tert-butyl(dimethyl)silyl]oxy}methyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidine-4-carboxylate
Ausbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

tert-Butyl 5-(benzyloxy)-6-methyl-2-(piperidin-4-ylmethyl)pyrimidine-4-carboxylate hydrochloride (1.0 g, 2.3 mmol), [(4′-bromobiphenyl-4-yl)methoxy](tert-butyl)dimethylsilane (0.92 g, 2.4 mmol), sodium tert-butoxide (0.67 g, 7.0 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (X-PHOS) (0.11 g, 0.23 mmol) and tris(dibenzylideneacetone)dipalladium (0.11 g, 0.12 mmol) were suspended in toluene (50 mL), followed by heating to reflux for 3 hours under a nitrogen atmosphere. The reaction solution was cooled to room temperature, and filtered with celite, and subsequently the filtrate was concentrated under reduced pressure. The resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate), and a fraction corresponding to the Rf value=0.50 (hexane/ethyl acetate=2/1) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (0.98 g, 1.4 mmol) as a yellow oil (yield 61%).

Aufarbeitung

  1. temperatureby heating
  2. temperatureto reflux for 3 hours under a nitrogen atmosphere
  3. filtrationfiltered with celite
  4. concentrationsubsequently the filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate)
  6. concentrationa fraction corresponding to the Rf value=0.50 (hexane/ethyl acetate=2/1) by thin layer chromatography was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-103fd202fdfb4d42ace795086a7ea547
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08785462B2

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