Potassium Carbonate → HCID 59860298, Verbindung

HRID 270705

Reaktionsgleichung

Reaktionsgleichung von HRID 270705
[NH2:1][C:2]1[C:7]([CH:8]=O)=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1.[NH2:12][C:13]1[C:14]([Cl:23])=[C:15]([CH2:20][C:21]#[N:22])[C:16]([Cl:19])=[CH:17][CH:18]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH2:12][C:13]1[C:14]([Cl:23])=[C:15]([C:20]2[C:21]([NH2:22])=[N:1][C:2]3[N:3]=[C:4]([S:10][CH3:11])[N:5]=[CH:6][C:7]=3[CH:8]=2)[C:16]([Cl:19])=[CH:17][CH:18]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 2957694-Amino-2-(methylsulfanyl)pyrimidine-5-carbaldehydeHCID 23185255HCID 23185255, Verbindung

Produkt 1

HCID 59860298HCID 59860298, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 4-amino-2-methylsulfanyl-pyrimidine-5-carbaldehyde (2.0 g, 11.82 mmol), (3-amino-2,6-dichloro-phenyl)-acetonitrile (2.85 g, 14.18 mmol) and K2CO3 (4.9 g, 35.49 mmol) in DMF (20 mL) is heated to 110° C. for 30 hours. The solution is cooled to room temperature and the solid is removed by filter paper and concentrated to give crude product. Flash silica gel column purification, eluting with CH2Cl2 (100%) gradient to CH2Cl2/MeOH (2N NH3) (100/7%), gives the title intermediate as a solid (3.31 g, 80.0%).

Aufarbeitung

  1. temperatureThe solution is cooled to room temperature
  2. customthe solid is removed
  3. filtrationby filter paper
  4. concentrationconcentrated
  5. customto give crude product
  6. customFlash silica gel column purification
  7. washeluting with CH2Cl2 (100%) gradient to CH2Cl2/MeOH (2N NH3) (100/7%)

Quellen und Nachweise

ORD-Eintrag
ord-e4f4a8f10e67450f8d1fa16affa1cd13
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449582B2

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