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

HRID 1924112Notes

Reaction equation

HRID 1924112 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 27995724-(Dimethoxymethyl)-2-methylpyrimidineYield 91.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
40 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-e4f679468da6435e90e93b8b381cd5bc
Source dataset
uspto-grants-2012_05
Patent number
US08178540B2

Reaction notes

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