Potassium Carbonate → 1-(4-Hydroxybutyl)-6-phenylthiothymine

HRID 1057247

Reaktionsgleichung

Reaktionsgleichung von HRID 1057247
[C:1]1([C:7]2[NH:12][C:11](=[S:13])[NH:10][C:9](=[O:14])[C:8]=2[CH3:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:16]([CH2:24][CH2:25][CH2:26][CH2:27]C1C=C(S([O-])(=O)=O)C=CC=1C)[Si](C(C)(C)C)(C)C.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[OH:16][CH2:24][CH2:25][CH2:26][CH2:27][N:12]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[C:8]([CH3:15])[C:9](=[O:14])[NH:10][C:11]1=[S:13]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 186710275-Methyl-6-phenyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-4-oneHCID 867490594-(t-Butyldimethylsiloxy)-butyl-p-toluenesulphonate

Produkt 1

HCID 541798301-(4-Hydroxybutyl)-6-phenylthiothymineAusbeute 4,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To 2 ml of dimethyl sulfoxide, 468 mg (2.0 mmol) of 6-phenythiothymine, 358 mg (1.0 mmol) of 4-(t-butyldimethylsiloxy)-butyl-p-toluenesulphonate and 276 mg (2.0 mmol) of potassium carbonate were added and heated to react for 4 hours at 80° C. The reaction mixture was concentrated under reduced pressure, added with methanol and filtered. The filtrate was concentrated under reduced pressure, added with 20 ml of tetrahydrofuran and 1 ml of 1N hydrochloric acid and stirred for 90 minutes. The reaction mixture was concentrated under reduced pressure and adsorbed on a silica gel column and eluted with 2% methanol/chloroform The eluate was concentrated and crystallized from acetone/hexane to obtain 12.0 mg of the target compound (Yield: 4%).

Aufarbeitung

  1. temperatureheated
  2. customto react for 4 hours at 80° C
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionadded with methanol
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. additionadded with 20 ml of tetrahydrofuran and 1 ml of 1N hydrochloric acid
  8. concentrationThe reaction mixture was concentrated under reduced pressure
  9. washeluted with 2% methanol/chloroform The eluate
  10. concentrationwas concentrated
  11. customcrystallized from acetone/hexane

Quellen und Nachweise

ORD-Eintrag
ord-907b2baf85be45e89b06298c744d836e
Quelldatensatz
uspto-grants-2003_02
Patentnummer
USRE037979E1

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