Water → HCID 178461553, Verbindung

HRID 876515Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 876515
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[N:3]=1.[CH3:17][C@H:18]1[O:23][C@@H:22]([CH3:24])[CH2:21][NH:20][CH2:19]1.CCN(C(C)C)C(C)C.O>CC(N(C)C)=O>[CH3:24][C@@H:22]1[O:23][C@H:18]([CH3:17])[CH2:19][N:20]([C:2]2[N:10]=[C:9]3[C:5]([N:6]=[CH:7][NH:8]3)=[C:4]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[N:3]=2)[CH2:21]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 6415002,6-Dimethylmorpholine, cis-HCID 32746034-(2-chloro-9H-purin-6-yl)morpholine

Produkt 1

HCID 178461553HCID 178461553, VerbindungAusbeute 98,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

To the solution of 2-chloro-6-morpholin-4-yl-9H-purine (1.5 g, 6.26 mmol) in DMA (5 mL) was added cis-2,6 dimethylmorpholine (1.42 g, 12.52 mmol), followed by DIPEA (2.1 mL, 12.02 mmol). The mixture was stirred at 130° C. for 40 hours. Upon completion of the reaction, the solution was poured into water. The aqueous layer was extracted with EtOAc three times. The combined organic layers were dried over Na2SO4, filtered and the solvent was removed under reduced pressure to provide 2-((2S,6R)-2,6-dimethyl-morpholin-4-yl)-6-morpholin-4-yl-9H-purine (1.96 g, 98%) as a yellow solid. LC/MS analysis method 7, mass (ES+) m/z 319.2 1HNMR (DMSO-d6): 12.37 (1H, s), 7.76 (1H, s), 4.38 (2H, d), 4.12 (4H, brs), 3.69 (4H, m), 3.54 (2H, m), 2.40 (2H, m), 1.14 (6H, d).

Aufarbeitung

  1. customUpon completion of the reaction
  2. extractionThe aqueous layer was extracted with EtOAc three times
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c26f0c6e375848d68d4ffe8108b07eda
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987257B2

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