Morpholine → Tert-butyl 2-chloro-4-morpholino-5H-pyrrolo[3,4-D]pyrimidine-6(7H)-carboxylate

HRID 1626536Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1626536
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][C:6]=2[N:7]=1.CCN(C(C)C)C(C)C.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.CCOC(C)=O>C(Cl)Cl.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[N:3]=[C:4]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[C:5]2[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][C:6]=2[N:7]=1

Komponenten

7

Edukt 4

HCID 8083MorpholineHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 17998715tert-Butyl 2,4-dichloro-5,7-dihydro-6H-pyrrolo(3,4-d)pyrimidine-6-carboxylate

Produkt 1

HCID 71540665Tert-butyl 2-chloro-4-morpholino-5H-pyrrolo[3,4-D]pyrimidine-6(7H)-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 2,4-dichloro-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate (1.00 g, 3.44 mmol) and DIPEA (0.672 mL, 3.86 mmol) at room temperature (20° C.) in DCM (7 mL) was added morpholine (0.33 mL, 3.86 mmol). After 2 h the reaction was diluted with DCM and Sat. NaHCO3. The organic layer was rinsed (brine), dried (anhydrous Na2SO4) and concentrated in vacuo. The desired product was isolated by flash chromatography (silica, 50 g, 0-50% EtOAc in petroleum ether (40-60) over 25 min) as a white solid (0.63 g, 1.85 mmol, 54% yield).

Aufarbeitung

  1. washThe organic layer was rinsed (brine)
  2. dry with materialdried (anhydrous Na2SO4)
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f7a472d6d3d249cf9f7201607216f693
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785457B2

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