Triphenylphosphine → 3-Butyl-8-chloro-1-[3-(1H-imidazol-4-yl)propyl]-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione

HRID 1097638Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1097638
[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([Cl:14])[N:10]([CH2:15][CH:16]=[CH2:17])[C:9]=2[C:8](=[O:18])[NH:7][C:6]1=[O:19])[CH2:2][CH2:3][CH3:4].[NH:20]1[CH:24]=[C:23]([CH2:25][CH2:26][CH2:27]O)[N:22]=[CH:21]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(COC(/N=N/C(OCC2C=CC=CC=2)=O)=O)=CC=1>C1COCC1>[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([Cl:14])[N:10]([CH2:15][CH:16]=[CH2:17])[C:9]=2[C:8](=[O:18])[N:7]([CH2:27][CH2:26][CH2:25][C:23]2[N:22]=[CH:21][NH:20][CH:24]=2)[C:6]1=[O:19])[CH2:2][CH2:3][CH3:4]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 5387121Dibenzyl azodicarboxylateHCID 592995823-butyl-8-chloro-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dioneHCID 178520509HCID 178520509, Verbindung

Produkt 1

HCID 1784563173-Butyl-8-chloro-1-[3-(1H-imidazol-4-yl)propyl]-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dioneAusbeute 55,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 3-butyl-8-chloro-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (2.8 g, 9.9 mmol) in anhydrous THF (60 ml) was treated with 3-(1H-imidazol-4-yl)-1-propanol (1.5 g, 12 mmol) in anhydrous THF (10 ml) and PPh3 (3.4 g, 13 mmol). DBAD (2.9 g, 13 mmol) was added in one portion and the mixture was left to stir at rt, under nitrogen for 18 h. The mixture was partitioned between EtOAc and H2O. The aqueous layer was extracted and washed with EtOAc. The organic layers were combined, washed with brine, dried (MgSO4) and concentrated. The crude product was purified by a silica SPE cartridge using a MeOH/EtOAc gradient (0.5%-7% MeOH). The product fractions were combined and concentrated by to give the title compound as a white solid (2.16 g, 55%).

Aufarbeitung

  1. waitthe mixture was left
  2. customThe mixture was partitioned between EtOAc and H2O
  3. extractionThe aqueous layer was extracted
  4. washwashed with EtOAc
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe crude product was purified by a silica SPE cartridge
  9. concentrationconcentrated by

Quellen und Nachweise

ORD-Eintrag
ord-2a3edd7364c945a1a4a1a99e81fef3a8
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143264B2

Notizen zur Reaktion

Wird geladen…