Methyl iodide → 6-Amino-4-furan-2-yl-2-methylsulfanyl-nicotinonitrile

HRID 1356048Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1356048
[NH2:1][C:2]1[NH:7][C:6](=[S:8])[C:5]([C:9]#[N:10])=[C:4]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[CH:3]=1.[CH3:16][O-].[Na+].CI>CO>[NH2:1][C:2]1[CH:3]=[C:4]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[C:5]([C:9]#[N:10])=[C:6]([S:8][CH3:16])[N:7]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 185073536-Amino-4-furan-2-yl-2-thioxo-1,2-dihydro-pyridine-3-carbonitrile

Produkt 1

HCID 185075176-Amino-4-furan-2-yl-2-methylsulfanyl-nicotinonitrileAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 150 mg (0.69 mmol) 6-amino-4-furan-2-yl-2-thioxo-1,2-dihydro-pyridine-3-carbonitrile in 3 ml methanol were added 0.13 ml (0.69 mmol) sodium methylate solution (5.4M in ethanol) and 0.04 ml (0.69 mmol) methyl iodide and the reaction mixture stirred at room temperature for 30 minutes. The reaction mixture was then concentrated in vacuo and the residue partitioned between dichloromethane and water. The organic phase was dried over sodium sulfate and concentrated in vacuo. The residue was triturated in ether to afford 113 mg (71%) 6-amino-4-furan-2-yl-2-methylsulfanyl-nicotinonitrile as a brown crystalline solid. ES-MS m/e (%): 232 (M+H+, 100).

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue partitioned between dichloromethane and water
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated in ether

Quellen und Nachweise

ORD-Eintrag
ord-1b3792b8994d4589aad7a26e533721d2
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586441B2

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