Isopropanol → N(6)-(2-(4-Chlorophenyl)bicyclo(2.2.2.)-octyl)(3)-adenosine

HRID 280509

Reaktionsgleichung

Reaktionsgleichung von HRID 280509
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]1[OH:13].[NH2:20][CH:21]1[CH:26]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[CH:25]2[CH2:34][CH2:35][CH:22]1[CH2:23][CH2:24]2.CN(C)C=O.C(O)(C)C>C(N(CC)CC)C>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([CH:26]2[CH:21]([NH:20][C:2]3[C:3]4[N:4]=[CH:5][N:6]([C:7]=4[N:8]=[CH:9][N:10]=3)[C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]3[OH:13])[CH:22]3[CH2:35][CH2:34][CH:25]2[CH2:24][CH2:23]3)=[CH:32][CH:31]=1

Komponenten

6

Edukt 4

HCID 3776IsopropanolHCID 6228DimethylformamideHCID 930036-Chloropurine ribosideHCID 128109192-Amino-3-p-chlorophenylbicyclo[2,2,2]octane

Produkt 1

HCID 173306N(6)-(2-(4-Chlorophenyl)bicyclo(2.2.2.)-octyl)(3)-adenosine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 28.6 g of 6-chloro-9(β-D-ribofuranosyl)-purine, 23.6 g of 2-amino-3-p-chlorophenylbicyclo[2,2,2]octane, 450 ml of dimethylformamide, 450 ml of isopropanol and 50 ml of triethylamine is left to stand at 20° for 4 days. The mixture is evaporated, the residue is dissolved in chloroform, the chloroform solution is washed with 1% aqueous acetic acid and evaporated again and the residue is triturated with ether to give N6 -[2-(4-chlorophenyl)-bicyclo[2,2,2]oct-3-yl]-adenosine (Ia). M.p.: 145° (decomposition). Rf: 0.41 (silica gel; CH2Cl2 :CH3OH 9:1).

Aufarbeitung

  1. waitis left
  2. customThe mixture is evaporated
  3. dissolutionthe residue is dissolved in chloroform
  4. washthe chloroform solution is washed with 1% aqueous acetic acid
  5. customevaporated again
  6. customthe residue is triturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-6638039075df404f8761cdfd25e24c5f
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04590180

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