Water → (+/-)-cis-3-[(6-Phenylfuro[2,3-d]pyrimidin-4-yl)amino]cyclohexanol

HRID 2189036Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2189036
Cl[C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1.CCN(C(C)C)C(C)C.[NH2:26][C@H:27]1[CH2:32][CH2:31][CH2:30][C@H:29]([OH:33])[CH2:28]1.O>CN(C=O)C>[C:11]1([C:9]2[O:8][C:4]3[N:5]=[CH:6][N:7]=[C:2]([NH:26][C@@H:27]4[CH2:32][CH2:31][CH2:30][C@H:29]([OH:33])[CH2:28]4)[C:3]=3[CH:10]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 117882853-Aminocyclohexanol, (1S,3S)-HCID 579464884-Chloro-6-phenylfuro[2,3-d]pyrimidine

Produkt 1

HCID 86653748(+/-)-cis-3-[(6-Phenylfuro[2,3-d]pyrimidin-4-yl)amino]cyclohexanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Heat a mixture of 4.0 g (17.34 mmol) of 4-chloro-6-phenylfuro[2,3-d]pyrimidine, 4.5 ml (26 mmol) of DIEA and 2.8 g of (+/−)-cis/trans-3-aminocyclohexanol (approx. 85% strength, approx. 20.8 mmol; approx. 3:1 cis/trans mixture; prepared according to J. Chem. Soc. Perkin Trans. I, 1994, 537) in 15 ml of DMF is heated to 120° C. overnight. After cooling, add the reaction mixture to water and extract three times with ethyl acetate. Wash the combined organic phases with saturated sodium chloride solution, dry over magnesium sulphate and concentrate under reduced pressure. Repeated stirring of the crude product with a mixture of methyl tert-butyl ether and dichloromethane enriches the product in the mother liquor. After concentrating the mother liquor, filter off the product with suction after crystallization from dichloromethane/methanol (10:1) and dry it under reduced pressure. 1.11 g (20.7% of theory) of the target product are obtained.

Aufarbeitung

  1. temperatureHeat
  2. temperatureAfter cooling
  3. extractionextract three times with ethyl acetate
  4. washWash the combined organic phases with saturated sodium chloride solution
  5. dry with materialdry over magnesium sulphate
  6. concentrationconcentrate under reduced pressure
  7. concentrationAfter concentrating the mother liquor
  8. filtrationfilter off the product with suction
  9. customafter crystallization from dichloromethane/methanol (10:1)
  10. customdry it under reduced pressure
  11. custom1.11 g (20.7% of theory) of the target product are obtained

Quellen und Nachweise

ORD-Eintrag
ord-f9cffe85dc554eb5b173dc332165bd8d
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324222B2

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