Sodium Cyanide → 4-Methylpyrimidine-2-carbonitrile

HRID 218027

Reaktionsgleichung

Reaktionsgleichung von HRID 218027
Cl[C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[C-:9]#[N:10].[Na+]>C(OCC)C.CN(C)C>[CH3:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:9]#[N:10])[N:7]=1

Komponenten

5

Edukt 2

HCID 8929Sodium CyanideHCID 116296072-Chloro-4-methylpyrimidine

Produkt 1

HCID 126843244-Methylpyrimidine-2-carbonitrileAusbeute 64,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1146TrimethylamineLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of 2-chloro-4-methylpyrimidine (3.00 g, 23.3 mmol; 3B Pharmachem International, China) in ethyl ether (24 mL) was added a solution of sodium cyanide (2.86 g, 58.3 mmol) in trimethylamine solution (1:3, trimethylamine:water, 24.0 mL). The reaction mixture was stirred at room temperature overnight. The aqueous layer was extracted with ethyl ether (3×20 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure to yield the title compound, 4-methyl-pyrimidine-2-carbonitrile (1.80 g; 64.8%), which was used in the next step without further purification. 1H NMR (400 MHz, D2O) δ 8.64 (d, J=5.4 Hz, 1H), 7.59 (d, J=5.5 Hz, 1H).

Aufarbeitung

  1. extractionThe aqueous layer was extracted with ethyl ether (3×20 mL)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-11577d72cb8e47d390396c7b1d4ba5e1
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198275B2

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