3,4-dihydro-2H-pyran → 6-Bromo-9-(tetrahydro-2H-pyran-2-YL)-9H-purine

HRID 510897Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 510897
[Br:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:23]1[CH:28]=[CH:27][CH2:26][CH2:25][CH2:24]1>C(Cl)(Cl)Cl>[Br:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:24]1[CH2:25][CH2:26][CH2:27][CH2:28][O:23]1

Komponenten

5

Edukt 3

HCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 178419477HCID 178419477, Verbindung

Produkt 1

HCID 583686166-Bromo-9-(tetrahydro-2H-pyran-2-YL)-9H-purineAusbeute 98,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A solution of 6-bromo-9H-purine (5.0 g, 25 mmol) and p-toluenesulfonic acid monohydrate (0.48 g, 2.5 mmol) in chloroform (100 mL) was cooled to 0° C., treated with dihydropyran (3.4 mL, 38 mmol) and stirred at room temperature for 1 hour. The reaction mixture was washed with saturated sodium bicarbonate, water and brine, dried with MgSO4, filtered, concentrated and purified on silica gel (eluting with 0-50% of ethyl acetate in hexanes) to give the desired product (7.0 g, 98%).

Aufarbeitung

  1. washThe reaction mixture was washed with saturated sodium bicarbonate, water and brine
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified on silica gel (eluting with 0-50% of ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-b68ebf6b2c1b4a4e85063eb7915cff49
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096600B2

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