Potassium Carbonate → 6-(3,5-Dimethoxy-phenyl)-8-ethyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-ylideneamine

HRID 1793878

Reaktionsgleichung

Reaktionsgleichung von HRID 1793878
[CH2:1]([NH:3][C:4]1[C:9]([CH:10]=O)=[CH:8][N:7]=[C:6]([S:12][CH3:13])[N:5]=1)[CH3:2].CO[C:16]1[CH:17]=[C:18]([CH2:24][C:25]#[N:26])[CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1.[C:27]([O-:30])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:23][O:22][C:20]1[CH:19]=[C:18]([C:24]2[C:25](=[NH:26])[N:3]([CH2:1][CH3:2])[C:4]3[N:5]=[C:6]([S:12][CH3:13])[N:7]=[CH:8][C:9]=3[CH:10]=2)[CH:17]=[C:16]([O:30][CH3:27])[CH:21]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 1394453,5-DimethoxyphenylacetonitrileHCID 107504444-(Ethylamino)-2-(methylthio)pyrimidine-5-carbaldehyde2×

Produkt 1

HCID 222201776-(3,5-Dimethoxy-phenyl)-8-ethyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-ylideneamineAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of the product of Example 3, 4-ethylamino-2-methylsulfanyl-pyrimidine-5-carboxaldehyde (37.0 g, 0.19 mol) and 3,5-dimethoxyphenylacetonitrile (37.0 g, 0.21 mol) in DMF (300 mL) was added portionwise anhydrous K2CO3 (130 g) with stirring. The reaction mixture was heated overnight at 105–110° C. and filtered hot. The insoluble salts were washed with DMF (100 mL), and water was added to the warm filtrate until the solution just turned turbid. Crystals developed upon seeding or inducement (scratching with a glass rod). The product was collected by filtration, washed with 100 mL DMF/H2O (25:75), washed with water, and dried in vacuo to afford 50.5 g (76%) of the titled compound. mp 93–95° C.

Aufarbeitung

  1. temperatureThe reaction mixture was heated overnight at 105–110° C.
  2. filtrationfiltered hot
  3. washThe insoluble salts were washed with DMF (100 mL), and water
  4. additionwas added to the warm filtrate until the solution just turned turbid
  5. filtrationThe product was collected by filtration
  6. washwashed with 100 mL DMF/H2O (25:75)
  7. washwashed with water
  8. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b253223e501e42c8b794043a5caa9902
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07022711B2

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