Acetamidine monohydrochloride → 4-(Dimethoxymethyl)-2-methylpyrimidine

HRID 1924112

Reaktionsgleichung

Reaktionsgleichung von HRID 1924112
Cl.[C:2]([NH2:5])(=[NH:4])[CH3:3].CN(C)[CH:8]=[CH:9][C:10](=O)[CH:11]([O:14][CH3:15])[O:12][CH3:13].C[O-].[Na+]>CO>[CH3:13][O:12][CH:11]([O:14][CH3:15])[C:10]1[CH:9]=[CH:8][N:5]=[C:2]([CH3:3])[N:4]=1

Komponenten

5

Edukt 3

HCID 67170Acetamidine monohydrochlorideHCID 27821454-(Dimethylamino)-1,1-dimethoxybut-3-en-2-oneHCID 10942334Sodium Methoxide

Produkt 1

HCID 27995724-(Dimethoxymethyl)-2-methylpyrimidineAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Acetamidine hydrochloride (3 mol) and 4-dimethylamino-1,1-dimethoxy-but-3-en-2-one (2 mol) were mixed in methanol (500 ml) and the reaction mixture was warmed to 40° C. A solution of sodium methoxide in methanol (558 g, 30%) was added quickly and a brown suspension was formed. The reaction mixture was heated under reflux for 2 h, cooled to room temperature overnight followed by evaporation of methanol under reduced pressure. The resulting residue was taken up in dichloromethane (500 ml) and washed several times with water (100 mL). The solvent was removed to give 307 g of black oil. The distillation of this oil gave a colourless liquid of boiling point 55-58° C. (0.5 mbar).

Aufarbeitung

  1. customa brown suspension was formed
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 2 h
  4. temperaturecooled to room temperature overnight
  5. customfollowed by evaporation of methanol under reduced pressure
  6. washwashed several times with water (100 mL)
  7. customThe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-e4f679468da6435e90e93b8b381cd5bc
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178540B2

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