6-(Phenylmethoxy)-9H-purin-2-amine → HCID 14154536, Verbindung

HRID 845035

Reaktionsgleichung

Reaktionsgleichung von HRID 845035
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1.[H-].[Na+].[H][H].C1(C)C=CC(S(O[CH2:33][CH2:34][CH2:35][CH:36]2[CH2:40][O:39][C:38]([CH3:42])([CH3:41])[O:37]2)(=O)=O)=CC=1>CN(C=O)C.CCOCC.C(O)(=O)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:33][CH2:34][CH2:35][CH:36]2[CH2:40][O:39][C:38]([CH3:42])([CH3:41])[O:37]2)=[C:4]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:3]=1

Komponenten

8

Edukt 4

HCID 45786-(Phenylmethoxy)-9H-purin-2-amineHCID 24758Sodium hydrideHCID 10757649HCID 10757649, VerbindungHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 14154536HCID 14154536, VerbindungAusbeute 25,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of 2.41 g (10 mmole) of 2-amino-6-benzyloxypurine [M. J. Robins and R. K. Robins, J. Org. Chem., 24, 2160 (1969)] in 24 ml of dry DMF was treated with 0.44 g (11 mmole) of sodium hydride (60% dispersion in oil). The mixture was stirred under nitrogen as hydrogen was evolved. After gas evolution had ceased and a clear solution had formed, a solution of 3.46 g (11 mmole) of (±)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)propyl p-toluene-sulfonate (prepared as above) in 2 ml of DMF was added. The mixture was stirred at 60° C. for 3 days. The cooled mixture was then neutralized with glacial acetic acid and concentrated in vacuo. The residue was taken up in ethyl acetate, filtered, re-concentrated and chromatographed on silica gel (elution with ethyl acetate). Evaporation of fractions containing clean product gave a residue which, on trituration with ether, yielded 975 mg (25%) of white crystals, mp 111°-112° C. The analytical batch, similarly prepared, had m.p. 115.5°-118°.

Aufarbeitung

  1. customa clear solution had formed
  2. concentrationconcentrated in vacuo
  3. filtrationfiltered
  4. concentrationre-concentrated
  5. customchromatographed on silica gel (elution with ethyl acetate)
  6. customEvaporation of fractions
  7. additioncontaining clean product
  8. customgave a residue which

Quellen und Nachweise

ORD-Eintrag
ord-7cabf6e2e6a64bd792398e990a961e79
Quelldatensatz
uspto-grants-1988_07
Patentnummer
US04755516

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