Water → 2-(4,6-Dimethoxypyrimidine-2-yl)acetonitrile

HRID 344576Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 344576
[C-:1]#[N:2].[Na+].Cl[CH2:5][C:6]1[N:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]([O:14][CH3:15])[N:7]=1.O>CS(C)=O>[C:1]([CH2:5][C:6]1[N:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]([O:14][CH3:15])[N:7]=1)#[N:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 8929Sodium CyanideHCID 109652792-(Chloromethyl)-4,6-dimethoxypyrimidine

Produkt 1

HCID 145806742-(4,6-Dimethoxypyrimidine-2-yl)acetonitrileAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel2×

Versuchsvorschrift

16.7 g of dried sodium cyanide are dissolved in 850 ml of dimethyl sulfoxide at 90° C. under N2 protective gas. At this temperature, 52.8 g of 2-chloromethyl-4,6-dimethoxypyrimidine, dissolved in 280 ml of dimethyl sulfoxide, are added dropwise over the course of 2 hours. Stirring is continued for 1 hour at 90° C., and the mixture is cooled to room temperature and poured into 300 ml of water. The aqueous phase is extracted seven times using ether, and the combined organic phases are washed using saturated aqueous sodium chloride solution, dried over magnesium sulfate and evaporated in a rotary evaporator. This gives 29.1 g of crude product, from which 2-cyanomethyl-4,6-dimethoxypyrimidine of melting point 65°-67° C. are obtained after column chromatography (SiO2 ; CH2Cl2 /CH3OH; 98.5/1.5).

Aufarbeitung

  1. additionare added dropwise over the course of 2 hours
  2. extractionThe aqueous phase is extracted seven times
  3. washthe combined organic phases are washed
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in a rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-3e2838a069f84763940e5d1b25a2f2c0
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05053072

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