Potassium Carbonate → 2-Amino-6,8-dichloro-9-(2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl)purine

HRID 846847

Reaktionsgleichung

Reaktionsgleichung von HRID 846847
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][C:7]([Cl:11])=[N:8]2)=[C:4]([Cl:12])[N:3]=1.Br[CH2:14][CH2:15][CH:16]1[CH2:21][O:20][C:19]([CH3:23])([CH3:22])[O:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([Cl:11])[N:8]2[CH2:14][CH2:15][CH:16]2[CH2:21][O:20][C:19]([CH3:23])([CH3:22])[O:18][CH2:17]2)=[C:4]([Cl:12])[N:3]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 1789881,3-Dioxane, 5-(2-bromoethyl)-2,2-dimethyl-HCID 54646776,8-Dichloro-9H-purin-2-amine

Produkt 1

HCID 198839912-Amino-6,8-dichloro-9-(2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl)purineAusbeute 44,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2-amino-6,8-dichloropurine (0.82 g), 5-bromoethyl-2,2-dimethyl-1,3-dioxan (0.9 g) and anhydrous potassium carbonate (0.83 g) in N,N-dimethylformamide (20 ml) was stirred at room temperature for 18 hours under dry nitrogen. The mixture was then filtered and the filtrate evaporated. The residue was purified by column chromatography on silica (100 g) [eluent 2% methanol-dichloromethane] to give 2-amino-6,8-dichloro-9-(2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl)purine (t.l.c. r.f. 0.50, 5% methanol-dichloromethane) as a pale solid (0.62 g, 45%). Recrystallisation from diethyl ether gave an off-white solid m.p. 149°-150° C.

Aufarbeitung

  1. filtrationThe mixture was then filtered
  2. customthe filtrate evaporated
  3. customThe residue was purified by column chromatography on silica (100 g) [eluent 2% methanol-dichloromethane]

Quellen und Nachweise

ORD-Eintrag
ord-a403aacc28a742d09c1c39cdb24ddfc7
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05138057

Verknüpfte Notizen

Wird geladen…