Hydrochloric Acid → HCID 67159887, Verbindung

HRID 2189121Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2189121
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][CH:12]=3)=[C:9]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1.[C:25]([O:29][C:30](=[O:39])[CH2:31][O:32][CH:33]1[CH2:37][CH:36]([OH:38])[CH:35]=[CH:34]1)([CH3:28])([CH3:27])[CH3:26].O.Cl>CN(C=O)C>[C:25]([O:29][C:30](=[O:39])[CH2:31][O:32][C@H:33]1[CH2:37][C@@H:36]([O:38][C:2]2[C:3]3[C:10]([C:11]4[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][CH:12]=4)=[C:9]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[O:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:35]=[CH:34]1)([CH3:28])([CH3:26])[CH3:27]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 580168974-Chloro-5-(4-ethylphenyl)-6-phenylfuro[2,3-d]pyrimidineHCID 76739653HCID 76739653, Verbindung

Produkt 1

HCID 67159887HCID 67159887, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Dissolve 390.7 mg (1.17 mmol) of 4-chloro-5-(4-ethylphenyl)-6-phenylfuro[2,3-d]pyrimidine and 250 mg (1.17 mmol) of cis-(+/−)-{[(4-hydroxycyclopent-2-en-1-yl]oxy}acetic acid tert-butyl ester in 0.95 ml of DMF, cool to 0° C. and add 0.58 ml (1.17 mmol) of phosphazene base P2-t-Bu (2 M solution in THF). After the end of the addition, warm the mixture to RT and stir for a further 1 h. Then add the reaction mixture to water, adjust to pH 7 with 1N hydrochloric acid and extract three times with dichloromethane. Combine the organic phases, wash with satd. sodium chloride solution, dry over magnesium sulphate and concentrate under reduced pressure. Isolate the crude product by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 20:1→5:1). 510 mg (85.3% of theory) of the target compound are obtained.

Aufarbeitung

  1. additionAfter the end of the addition
  2. temperaturewarm the mixture to RT
  3. extractionextract three times with dichloromethane
  4. washwash with satd
  5. dry with materialsodium chloride solution, dry over magnesium sulphate
  6. concentrationconcentrate under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b4ea59f54aa8433c96d6fd36f940b1c9
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324222B2

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