1,8-Diazabicyclo(5.4.0)undec-7-ene → 8-cyclohexyl-5-hydroxy-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 2386672Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2386672
C1CCN2C(=NCCC2)CC1.C([O:14][C:15](=O)[CH2:16][C:17]([C:19]1[C:20]([NH:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[N:21][C:22]([S:25][CH3:26])=[N:23][CH:24]=1)=[O:18])C.CCN(C(C)C)C(C)C>>[CH:28]1([N:27]2[C:20]3[N:21]=[C:22]([S:25][CH3:26])[N:23]=[CH:24][C:19]=3[C:17]([OH:18])=[CH:16][C:15]2=[O:14])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Komponenten

4

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81531DiisopropylethylamineHCID 579294743-(4-Cyclohexylamino-2-methylsulfanyl-pyrimidin-5-yl)-3-oxo-propionic acid ethyl ester

Produkt 1

HCID 579294838-cyclohexyl-5-hydroxy-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-oneAusbeute 107,2 %

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

DBU (11.05 mL) was added dropwise, under argon atmosphere, to a mixture of 3-(4-cyclohexylamino-2-methylsulfanyl-pyrimidin-5-yl)-3-oxo-propionic acid ethyl ester (21.5 g) and DIPEA (85 mL), and the resulting mixture heated at 125° C. for 1 h, then stirred at RT overnight. The volatiles were evaporated under reduced pressure, and the residue was diluted with EtOAc and HCl (1 M aq). The solid residue was collected by filtration, the organic layer was separated, and the aqueous layer was extracted 3× with EtOAc. The combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure. The combined solids were washed 3× with NaHSO4 (aq 10%), twice with water, hexane (8×100 mL), and a 2:1 mixture of hexane and EtOAc (4×100 mL) to give, after drying under reduced pressure, 19.9 g (99% yield) of 8-cyclohexyl-5-hydroxy-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one without further purifications.

Aufarbeitung

  1. customThe volatiles were evaporated under reduced pressure
  2. additionthe residue was diluted with EtOAc and HCl (1 M aq)
  3. filtrationThe solid residue was collected by filtration
  4. customthe organic layer was separated
  5. extractionthe aqueous layer was extracted 3× with EtOAc
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. washThe combined solids were washed 3× with NaHSO4 (aq 10%)
  10. additiontwice with water, hexane (8×100 mL), and a 2:1 mixture of hexane and EtOAc (4×100 mL)
  11. customto give

Quellen und Nachweise

ORD-Eintrag
ord-4387e525ac6b47859e1bdc9ef60a3ee3
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08268840B2

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