Tetrahydrofuran → 8-(2-Chloro-5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-8-azabicyclo[3.2.1]octan-3-ol

HRID 928619

Reaktionsgleichung

Reaktionsgleichung von HRID 928619
O1CCCC1.C(N(CC)CC)C.[Cl:13][C:14]1[N:15]=[C:16](Cl)[C:17]2[C:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:21][S:20][C:18]=2[N:19]=1.[CH:30]12[NH:37][CH:34]([CH2:35][CH2:36]1)[CH2:33][CH:32]([OH:38])[CH2:31]2>O.C(OCC)(=O)C>[Cl:13][C:14]1[N:15]=[C:16]([N:37]2[CH:30]3[CH2:36][CH2:35][CH:34]2[CH2:33][CH:32]([OH:38])[CH2:31]3)[C:17]2[C:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:21][S:20][C:18]=2[N:19]=1

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 681478-Azabicyclo[3.2.1]octan-3-olHCID 127242282,4-Dichloro-5-phenylthieno(2,3-d)pyrimidine

Produkt 1

HCID 895795888-(2-Chloro-5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-8-azabicyclo[3.2.1]octan-3-olAusbeute 95,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Tetrahydrofuran (2 mL) and triethylamine (0.10 mL, 0.71 mmol) were added to 2,4-dichloro-5-phenyl-thieno[2,3-d]pyrimidine (100 mg, 0.356 mmol) and 8-azabicyclo[3.2.1]octan-3-ol (68 mg, 0.53 mmol). The mixture was stirred overnight at room temperature. Ethyl acetate (2 mL) and water (2 mL) were added and the layers were separated. The aqueous was extracted with ethyl acetate (2×2 mL). The combined organic layers were dried (magnesium sulfate), filtered and evaporated to give a brown solid (127 mg). This was purified by silica chromatography (10 g cartridge; eluent petroleum ether 40-60/ethyl acetate 0 to 30%; all output collected). One set of fractions was identified and the relevant fractions were combined and evaporated to give a brown solid (83 mg). This was purified again by LCUV (acidic method 1) to give the target compound as a white solid (44 mg). m/z [M+H]+372.0/373.9. Retention time 4.74 min (LCMS method+ve 6 min).

Aufarbeitung

  1. customthe layers were separated
  2. extractionThe aqueous was extracted with ethyl acetate (2×2 mL)
  3. dry with materialThe combined organic layers were dried (magnesium sulfate)
  4. filtrationfiltered
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-641d821350604458831a0a0cddebb5c9
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290511B2

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