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Dichloromethane → 8-(Tert-butyldimethylsilyloxy)-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-4-amine

HRID 336138
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 336138
C12BC(CCC1)CCC2.Br[C:11]1[N:20]([CH2:21][CH:22]([O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[CH:23]=[CH2:24])[C:14]2[N:15]=[CH:16][N:17]=[C:18]([NH2:19])[C:13]=2[C:12]=1[C:33]1[CH:34]=[N:35][C:36]2[C:41]([CH:42]=1)=[CH:40][CH:39]=[CH:38][CH:37]=2.[OH-].[Na+].ClCCl>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[Si:26]([O:25][CH:22]1[CH2:23][CH2:24][C:11]2[N:20]([C:14]3[N:15]=[CH:16][N:17]=[C:18]([NH2:19])[C:13]=3[C:12]=2[C:33]2[CH:34]=[N:35][C:36]3[C:41]([CH:42]=2)=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:21]1)([C:29]([CH3:32])([CH3:30])[CH3:31])([CH3:27])[CH3:28]
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Komponenten

8

Edukt 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 867112776-bromo-7-(2-(tert-butyldimethylsilyloxy)-3-butenyl)-5-(quinolin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Produkt 1

HCID 867112798-(Tert-butyldimethylsilyloxy)-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 0.5 M 9-borabicyclo[3.3.1]nonane in THF (50 ml) was added to a solution of 6-bromo-7-(2-(tert-butyldimethylsilyloxy)-3-butenyl)-5-(quinolin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (2.26 g) obtained in Step 6 in THF (30 ml) under ice-cooling. The mixture was stirred at room temperature for 4 hours. After slowly adding a 3 N aqueous sodium hydroxide solution (19.5 ml) to the reaction mixture at room temperature, a [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (676 mg) was added to the reaction mixture. The mixture was stirred under a nitrogen atmosphere at 70° C. for 4 hours. After cooling, the reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain the title compound as a yellow, oily substance (778 mg).

Aufarbeitung

  1. temperaturecooling
  2. stirringThe mixture was stirred under a nitrogen atmosphere at 70° C. for 4 hours
  3. temperatureAfter cooling
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-a9bc362653ec469baf6a6c1bb9eacbf3
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08889666B2

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