Cyclopropylamine → [(2R,4R)-4-[2-amino-6-(cyclopropylamino)purin-9-yl]-1,3-dioxolan-2-yl]methanol

HRID 2118090Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2118090
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@H:11]2[CH2:15][O:14][C@@H:13]([CH2:16][OH:17])[O:12]2)=[C:4](Cl)[N:3]=1.[CH:19]1([NH2:22])[CH2:21][CH2:20]1>C(O)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@H:11]2[CH2:15][O:14][C@@H:13]([CH2:16][OH:17])[O:12]2)=[C:4]([NH:22][CH:19]2[CH2:21][CH2:20]2)[N:3]=1

Komponenten

4

Edukt 2

HCID 69828CyclopropylamineHCID 454987HCID 454987, Verbindung

Produkt 1

HCID 485995[(2R,4R)-4-[2-amino-6-(cyclopropylamino)purin-9-yl]-1,3-dioxolan-2-yl]methanolAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

[4(R)-(2-Amino-6-chloro-purin-9-yl)-[1,3]dioxolan-2(R)-yl]-methanol (1.2 kg, 4.5 moles), ethanol (15.2 L) and cyclopropylamine (756 g) were refluxed under nitrogen for 16 hours. The reaction was monitored for completion by HPLC. Once completed the reaction mixture was hot-filtered and allowed to cool to 0° C. slowly. The solids were filtered and subsequently recrystallized from ethanol to give [4(R)-(2-Amino-6-cyclopropylamino-purin-9-yl)-[1,3]dioxolan-2(R)-yl]-methanol (1.0 kg, 77%).

Aufarbeitung

  1. filtrationwas hot-filtered
  2. filtrationThe solids were filtered
  3. customsubsequently recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-7804342d7d56448e814b975f7d1e1f09
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07442813B2

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