1-Cyclopentyl-3-(2,6-difluoro-3,5-dimethoxyphenyl)-7-(methylsulfinyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one → 1-Cyclopentyl-3-(2,6-difluoro-3,5-dimethoxy-phenyl)-7-(4-hydroxy-cyclohexylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

HRID 459969Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 459969
[CH:1]1([N:6]2[C:11]3=[N:12][C:13](S(C)=O)=[N:14][CH:15]=[C:10]3[CH2:9][N:8]([C:19]3[C:24]([F:25])=[C:23]([O:26][CH3:27])[CH:22]=[C:21]([O:28][CH3:29])[C:20]=3[F:30])[C:7]2=[O:31])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:32][C@H:33]1[CH2:38][CH2:37][C@H:36]([OH:39])[CH2:35][CH2:34]1>>[CH:1]1([N:6]2[C:11]3=[N:12][C:13]([NH:32][CH:33]4[CH2:38][CH2:37][CH:36]([OH:39])[CH2:35][CH2:34]4)=[N:14][CH:15]=[C:10]3[CH2:9][N:8]([C:19]3[C:24]([F:25])=[C:23]([O:26][CH3:27])[CH:22]=[C:21]([O:28][CH3:29])[C:20]=3[F:30])[C:7]2=[O:31])[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

3

Edukt 2

HCID 184448441-Cyclopentyl-3-(2,6-difluoro-3,5-dimethoxyphenyl)-7-(methylsulfinyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-oneHCID 178511715HCID 178511715, Verbindung

Produkt 1

HCID 103688021-Cyclopentyl-3-(2,6-difluoro-3,5-dimethoxy-phenyl)-7-(4-hydroxy-cyclohexylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-oneAusbeute 88 %

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

To a solution of 0.511 g (1.13 mmol) of 1-cyclopentyl-3-(2,6-difluoro-3,5-dimethoxy-phenyl)-7-methylsulfinyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one was added 0.39 g (3.39 mmol) of trans-4-aminocyclohexanol. The resulting mixture was heated at 1 10° C. oil bath temperature for 2 days under N2 atmosphere. The dioxane was evaporated. The crude product was purified by medium-pressure chromatography eluting with 20:1 dichloromethane/methanol to give 0.50 g (88%) of title compound: mp 208° C.–212° C. (dec). MS (APCI) (m+1)/z 504.2.

Aufarbeitung

  1. customThe dioxane was evaporated
  2. customThe crude product was purified by medium-pressure chromatography
  3. washeluting with 20:1 dichloromethane/methanol

Quellen und Nachweise

ORD-Eintrag
ord-2ada8be818e34bb78da4b322c6d198e6
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07196090B2

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