Ammonia → HCID 10243640, Verbindung

HRID 1885366Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1885366
[NH3:1].[NH2:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[C@H:12]2[CH2:16][C@@H:15]([CH2:17][OH:18])[CH:14]=[CH:13]2)=[C:5](Cl)[N:4]=1>CO>[NH2:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[C@H:12]2[CH2:16][C@@H:15]([CH2:17][OH:18])[CH:14]=[CH:13]2)=[C:5]([NH2:1])[N:4]=1

Komponenten

4

Edukt 2

HCID 222AmmoniaHCID 11777654(1R,4S)-4-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol

Produkt 1

HCID 10243640HCID 10243640, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

Liquid ammonia is passed into a solution of cis-(±)-2-amino-6-chloro-9-[4-(hydroxymethyl)-2-cyclopenten-1-yl]-9H-purine (0.265 g, 1 mmol) in methanol (10 mL) at -80° C. in a bomb. The bomb is sealed and heated at 75° C. for 48 hours. The bomb is cooled to room temperature and the ammonia and methanol are evaporated. The residue is purified by silica gel chromatography using 15:1 chloroform methanol as eluent to give cis-(±)-2,6-diamino-9-[4-(hydroxymethyl)-2-cyclo-penten-1-yl]-9H-purine (0.196 g, 80%). M.pt. 152°-155° C. MS (30 ev, 200° C.): m/e 246 (M+), 229 (M+-17), 216 (M+-30).

Aufarbeitung

  1. customThe bomb is sealed
  2. temperatureThe bomb is cooled to room temperature
  3. customthe ammonia and methanol are evaporated
  4. customThe residue is purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-04bc2087409a45caa590302b58a00f49
Quelldatensatz
uspto-grants-1992_09
Patentnummer
US05144034

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