StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Triphenylphosphine → 8-Chloro-3-pentyl-7-(2-propen-1-yl)-1-[3-(1H-pyrazol-4-yl)propyl]-3,7-dihydro-1H-purine-2,6-dione

HRID 1097634
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1097634
[CH2:1]([N:6]1[C:14]2[N:13]=[C:12]([Cl:15])[N:11]([CH2:16][CH:17]=[CH2:18])[C:10]=2[C:9](=[O:19])[NH:8][C:7]1=[O:20])[CH2:2][CH2:3][CH2:4][CH3:5].[NH:21]1[CH:25]=[C:24]([CH2:26][CH2:27][CH2:28]O)[CH:23]=[N:22]1.N(C(OCC1C=CC=CC=1)=O)=NC(OCC1C=CC=CC=1)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[Cl:15][C:12]1[N:11]([CH2:16][CH:17]=[CH2:18])[C:10]2[C:9](=[O:19])[N:8]([CH2:28][CH2:27][CH2:26][C:24]3[CH:25]=[N:21][NH:22][CH:23]=3)[C:7](=[O:20])[N:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[C:14]=2[N:13]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 755571,2-Bis(phenylmethyl) 1,2-diazenedicarboxylateHCID 35783843-(1H-pyrazol-4-yl)propan-1-olHCID 592995577-Allyl-8-chloro-3-pentyl-1H-purine-2,6(3H,7H)-dione

Produkt 1

HCID 593958038-Chloro-3-pentyl-7-(2-propen-1-yl)-1-[3-(1H-pyrazol-4-yl)propyl]-3,7-dihydro-1H-purine-2,6-dione
Ausbeute 42,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

3-Pentyl-8-chloro-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (5 g, 16.86 mmol) and 3-(1H-pyrazol-4-yl)propan-1-ol (2.12 g, 16.8 mmol) were stirred in dry THF (150 ml) at 3° C. Dibenzyl azodicarboxylate (10.05 g, 33.7 mmol) was added followed by the dropwise addition of triphenylphosphine (8.83 g, 33.7 mmol) in dry THF (70 ml). The mixture was allowed to warm to it and stirred for 18 h. Water (1 ml) was added and the solvents evaporated. The residue was taken up in Et2O (200 ml) from which a white solid, mostly triphenylphosphine oxide, crystallised and was filtered off. The filtrate was concentrated and further by-products crystallised from ether-cyclohexane. The remaining filtrate was concentrated (19.2 g) and purified on a Biotage™ system (400 g) eluting with EtOAc-cyclohexane (2:1) to afford the title compound as a white solid (2.89 g).

Aufarbeitung

  1. temperatureto warm to it
  2. customthe solvents evaporated
  3. customcrystallised
  4. filtrationwas filtered off
  5. concentrationThe filtrate was concentrated
  6. customfurther by-products crystallised from ether-cyclohexane
  7. concentrationThe remaining filtrate was concentrated (19.2 g)
  8. custompurified on a Biotage™ system (400 g)
  9. washeluting with EtOAc-cyclohexane (2:1)

Quellen und Nachweise

ORD-Eintrag
ord-a351c52f866a4ef3827555a2cc86e10d
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08143264B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion