Sodium Hydroxide → HCID 49854610, Verbindung

HRID 80631

Reaktionsgleichung

Reaktionsgleichung von HRID 80631
[N:1]1([C:7]2[N:8]=[C:9]3[NH:17][C@H:16]([C:18]([F:21])([F:20])[F:19])[CH2:15][CH2:14][N:10]3[C:11](=[O:13])[CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[OH-].[Na+].Br[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=1>C1(C)C=CC=CC=1.O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[Cl:33][C:29]1[CH:28]=[C:27]([CH2:26][CH2:25][N:17]2[C:9]3=[N:8][C:7]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[CH:12][C:11](=[O:13])[N:10]3[CH2:14][CH2:15][C@H:16]2[C:18]([F:20])([F:21])[F:19])[CH:32]=[CH:31][CH:30]=1

Komponenten

8

Edukt 3

HCID 14798Sodium HydroxideHCID 1401401-(2-Bromoethyl)-3-chlorobenzeneHCID 136238743(S)-8-(Morpholin-4-yl)-2-(trifluoromethyl)-1,2,3,4-tetrahydropyrimido[1,2-a]pyrimidin-6-one

Produkt 1

HCID 49854610HCID 49854610, VerbindungAusbeute 19,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The product is prepared according to the procedure described in Example 40, using 150 mg of (8S)-2-(morpholin-4-yl)-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4 H-pyrimido[1,2-a]pyrimidin-4-one in 2.5 ml of toluene are added 296 mg of sodium hydroxide in 2.5 ml of water, 33 mg of tetrabutylammonium hydrogen sulphate and 216 mg of 1-(2-bromoethyl)-3-chlorobenzene. After 44 hours at 60° C. After cooling, the reaction mixture is diluted with ethyl acetate. The organic phase is separated and the aqueous phase is extracted with ethyl acetate. The combined organic phases are concentrated to dryness under reduced pressure and the residue is purified by preparative HPLC/MS (Method D). 42 mg of (8S)-9-[2-(3-chloro-phenyl)ethyl]-2-(morpholin-4-yl)-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4 H-pyrimido[1,2-a]pyrimidin-4-one are thus obtained, the characteristics of which are the following:

Aufarbeitung

  1. customThe product is prepared
  2. temperatureAfter cooling
  3. customThe organic phase is separated
  4. extractionthe aqueous phase is extracted with ethyl acetate
  5. concentrationThe combined organic phases are concentrated to dryness under reduced pressure
  6. customthe residue is purified by preparative HPLC/MS (Method D)

Quellen und Nachweise

ORD-Eintrag
ord-324f1ced10c6442d886e75302abf13e7
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846670B2

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