Methanol → Methyl 2-methoxy-6-methylpyrimidine-4-carboxylate

HRID 1109977Notes

Reaction equation

HRID 1109977 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4]([CH3:12])[N:3]=1.[Na].[CH3:14][OH:15]>>[CH3:14][O:15][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4]([CH3:12])[N:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 2736835Methyl 2-chloro-6-methylpyrimidine-4-carboxylateHCID 5360545Sodium

Product 1

HCID 19018471Methyl 2-methoxy-6-methylpyrimidine-4-carboxylate

Procedure

30.0 g of methyl 2-chloro-6-methylpyrimidine-4-carboxylate are added to a solution of 4.2 g of sodium in 100 ml of methanol. The mixture is heated under reflux for 2 h and concentrated under reduced pressure, and the residue is taken upon in dichloromethane/water. The organic phase is separated off and the aqueous solution is extracted a further five times using dichloromethane. The combined organic extracts are dried over sodium sulfate and the solvent is distilled off under reduced pressure. 25.5 g of methyl 2-methoxy-6-methylpyrimidine-4-carboxylate of melting point 101°-103° C. are obtained in this way.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 2 h
  3. concentrationconcentrated under reduced pressure
  4. customThe organic phase is separated off
  5. extractionthe aqueous solution is extracted a further five times
  6. dry with materialThe combined organic extracts are dried over sodium sulfate
  7. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-c76daee0866c41d6bccd5a0e0699749a
Source dataset
uspto-grants-1994_06
Patent number
US05324710

Reaction notes

Loading…