Potassium Carbonate → 4-[(3R)-3-Methyl-4-(1-methyl-6-oxo-1,6-dihydro-[4,4']bipyrimidinyl-2-yl)-piperazin-1-yl]-benzonitrile

HRID 1045695Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1045695
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][N:10]=2)[N:4]=[C:3]1[N:15]1[CH2:20][CH2:19][NH:18][CH2:17][C@H:16]1[CH3:21].F[C:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>>[CH3:21][C@H:16]1[N:15]([C:3]2[N:2]([CH3:1])[C:7](=[O:8])[CH:6]=[C:5]([C:9]3[CH:14]=[CH:13][N:12]=[CH:11][N:10]=3)[N:4]=2)[CH2:20][CH2:19][N:18]([C:23]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=2)[CH2:17]1

Komponenten

4

Edukt 3

HCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 250045961-methyl-2-((2R)-2-methyl-piperazin-1-yl)-1H-[4,4']bipyrimidinyl-6-one

Produkt 1

HCID 578700144-[(3R)-3-Methyl-4-(1-methyl-6-oxo-1,6-dihydro-[4,4']bipyrimidinyl-2-yl)-piperazin-1-yl]-benzonitrileAusbeute 84 %

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a stirred solution of 1-Methyl-2-((2R)-2-methyl-piperazin-1-yl)-1H-[4,4′]bipyrimidinyl-6-one (1.50 g, 5.24 mmol) in dimethyl sulufoxide (10.0 ml) was added 4-fluorobenzonitrile (1.27 g, 10.5 mmol), potassium carbonate (2.90 g, 21.0 mmol), and the reaction mixture was stirred for 12 hours at 120° C. The reaction was quenched with water, the aqueous layer was extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate, and concentrated in vacuo. After removal of the solvent, the precipitate was filtered, washed with ether, and dried to give 4-[(3R)-3-Methyl-4-(1-methyl-6-oxo-1,6-dihydro-[4,4′]bipyrimidinyl-2-yl)-piperazin-1-yl]-benzonitrile (1.70 g, 4.39 mmol, 84%) as pale yellow crystals.

Aufarbeitung

  1. customThe reaction was quenched with water
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customAfter removal of the solvent
  7. filtrationthe precipitate was filtered
  8. washwashed with ether
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-3ce368620c184cd08e33686fe95d4a7a
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569294B2

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