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3,4-dihydro-2H-pyran → HCID 90402714, Verbindung

HRID 2200534
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2200534
[Br:1][C:2]1[N:10]([CH2:11][CH3:12])[C:9]2[C:8](=[O:13])[N:7]([CH2:14][CH2:15][CH2:16][OH:17])[C:6](=[O:18])[N:5]([CH3:19])[C:4]=2[N:3]=1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1.[O:37]1[CH:42]=[CH:41][CH2:40][CH2:39][CH2:38]1>C(Cl)Cl>[Br:1][C:2]1[N:10]([CH2:11][CH3:12])[C:9]2[C:8](=[O:13])[N:7]([CH2:14][CH2:15][CH2:16][O:17][CH:38]3[CH2:39][CH2:40][CH2:41][CH2:42][O:37]3)[C:6](=[O:18])[N:5]([CH3:19])[C:4]=2[N:3]=1
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Komponenten

5

Edukt 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 90402526HCID 90402526, Verbindung

Produkt 1

HCID 90402714HCID 90402714, VerbindungAusbeute 76,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 8-bromo-7-ethyl-1-(3-hydroxypropyl)-3-methyl-1H-purine-2,6(3H,7H)-dione (0.4 g, 1.2 mmol) in DCM (10 mL) was added PPTS (27 mg, 0.1 mmol); then dihydropyran (0.15 g, 1.8 mmol) was added dropwise at 0° C. The mixture was stirred at room temperature overnight. The mixture was partitioned between DCM and water. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to give a crude product which was purified by a column chromatography eluting with petroleum ether/ethyl acetate (3:1) to give 8-bromo-7-ethyl-3-methyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1H-purine-2,6(3H,7H)-dione (0.38 g, 76.9% yield) as white solid. LCMS retention time 1.871 min; LCMS MH+-THP 331.

Aufarbeitung

  1. customThe mixture was partitioned between DCM and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude product which
  7. customwas purified by a column chromatography
  8. washeluting with petroleum ether/ethyl acetate (3:1)

Quellen und Nachweise

ORD-Eintrag
ord-75a95dcd9133467ea10575f91659d702
Quelldatensatz
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09359359B2

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