Water → 4-chloro-2-(N-cyano-N-methylamino)-6-[(4-methyl)-piperidin-1-yl]-5-phenylpyrimidine

HRID 1766587Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1766587
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6]([N:14]2[CH2:19][CH2:18][CH:17]([CH3:20])[CH2:16][CH2:15]2)[N:5]=[C:4]([NH:21][C:22]#[N:23])[N:3]=1.O.[C:25](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[C:6]([N:14]2[CH2:19][CH2:18][CH:17]([CH3:20])[CH2:16][CH2:15]2)[N:5]=[C:4]([N:21]([C:22]#[N:23])[CH3:25])[N:3]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 857987184-chloro-2-(N-cyanoamino)-6-[(4-methyl)-piperidin-1-yl]-5-phenylpyrimidine

Produkt 1

HCID 223254994-chloro-2-(N-cyano-N-methylamino)-6-[(4-methyl)-piperidin-1-yl]-5-phenylpyrimidineAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-chloro-2-(N-cyanoamino)-6-[(4-methyl)-piperidin-1-yl]-5-phenylpyrimidine (0.1 g, 0.305 mmol) in dimethylformamide (4 ml) at room temperature was added water (2 ml) followed by potassium carbonate (0.084 g, 0.61 mmol) and the resulting suspension was warmed gently to afford a clear solution. To the cooled solution was then added methyl iodide (0.076 ml, 1.22 mmol) and the reaction mixture stirred at room temperature for 2.5 hours. The reaction was then quenched by the addition of saturated aqueous ammonium chloride solution (40 ml). After adding ethyl acetate (40 ml) the biphasic mixture was stirred for 5 minutes. The organic phase was then separated, washed with saturated brine (50 ml), dried over magnesium sulfate and concentrated in vacuo to afford a yellow syrup. The crude product was chromatographed an silica gel eluting with 90:10 v/v hexane: ethyl acetate to afford 0.09 g (87% yield) of the title compound as a colorless syrup.

Aufarbeitung

  1. temperaturethe resulting suspension was warmed gently
  2. customto afford a clear solution
  3. customThe reaction was then quenched by the addition of saturated aqueous ammonium chloride solution (40 ml)
  4. additionAfter adding ethyl acetate (40 ml) the biphasic mixture
  5. customThe organic phase was then separated
  6. washwashed with saturated brine (50 ml)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customto afford a yellow syrup
  10. customThe crude product was chromatographed an silica gel eluting with 90:10 v/v hexane

Quellen und Nachweise

ORD-Eintrag
ord-65fe74b011584203987b42888db4e151
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07230104B2

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