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Water → cis-1-{[6-(4,4-Dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}pyrrolidine-3,4-diol

HRID 2171811
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2171811
CS(O[CH2:6][C:7]1[C:8]2[CH:16]=[C:15]([CH:17]3[CH2:22][CH2:21][C:20]([CH3:24])([CH3:23])[CH2:19][CH2:18]3)[S:14][C:9]=2[N:10]=[C:11]([CH3:13])[N:12]=1)(=O)=O.Cl.[NH:26]1[CH2:30][C@H:29]([OH:31])[C@H:28]([OH:32])[CH2:27]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:23][C:20]1([CH3:24])[CH2:21][CH2:22][CH:17]([C:15]2[S:14][C:9]3[N:10]=[C:11]([CH3:13])[N:12]=[C:7]([CH2:6][N:26]4[CH2:30][C@H:29]([OH:31])[C@H:28]([OH:32])[CH2:27]4)[C:8]=3[CH:16]=2)[CH2:18][CH2:19]1
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Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 21970171(3S,4R)-pyrrolidine-3,4-diol hydrochlorideHCID 118023751[6-(4,4-Dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl methanesulfonate

Produkt 1

HCID 118023762cis-1-{[6-(4,4-Dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}pyrrolidine-3,4-diol
Ausbeute 8,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A suspension of [6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl methanesulfonate (100 mg), cis-pyrrolidine-3,4-diol hydrochloride (57 mg), and K2CO3 (75 mg) in DMF (3 mL) was stirred at 50° C. for 12 hours. The reaction mixture was cooled to room temperature, and water was added thereto, followed by extraction with EtOAc. The organic layer was dried over MgSO4 and then concentrated under reduced pressure. The residue was purified by silica gel column (chloroform/MeOH). The obtained purified product was suspended in IPE, and the precipitate was collected by filtration to obtain cis-1-{[6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]methyl}pyrrolidine-3,4-diol (9 mg).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionfollowed by extraction with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column (chloroform/MeOH)
  6. customThe obtained purified product
  7. filtrationthe precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-1421a5473a564f64af0dde8e02e88006
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09051339B2

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