Tyramine → 4-(2-((2-Chloro-9-isopropyl-9H-purin-6-yl)amino)ethyl)phenol

HRID 1422475Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1422475
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]([CH3:13])[CH3:12])=[C:4](Cl)[N:3]=1.[NH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1.C(N(CC)CC)C>CC(O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]([CH3:13])[CH3:12])=[C:4]([NH:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)[N:3]=1

Komponenten

5

Edukt 3

HCID 5610TyramineHCID 8471TriethylamineHCID 112184902,6-dichloro-9-(propan-2-yl)-9H-purine

Produkt 1

HCID 755299704-(2-((2-Chloro-9-isopropyl-9H-purin-6-yl)amino)ethyl)phenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

2,6-dichloro-9-isopropyl-9H-purine (500 g) was added in portions to a stirred mixture of tyramine (593 g), triethylamine (262 g), and i-PrOH (5.0 L) at 50° C. The mixture was stirred at that temperature for 4 hr, then the reaction mixture was concentrated. The residue was taken up in isopropyl acetate (6.0 L) and was washed with 20% citric acid solution (2.0 L) and water (2.0 L). The organic layer was concentrated to dryness, then was taken up in ethanol (2.0 L) and again concentrated to dryness. The crude solid was crystallized from ethanol (3.2 L) to provide the title compound as a solid.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated
  2. washwas washed with 20% citric acid solution (2.0 L) and water (2.0 L)
  3. concentrationThe organic layer was concentrated to dryness
  4. concentrationagain concentrated to dryness
  5. customThe crude solid was crystallized from ethanol (3.2 L)

Quellen und Nachweise

ORD-Eintrag
ord-21a1f1f5ab624e4c9d0d538b6c42ea35
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927281B2

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