Sodium Hydroxide → 4-Methoxy-6-methylpyrimidine-2-carboxylic acid

HRID 2081917Notes

Reaction equation

HRID 2081917 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[C:9]([CH3:11])[N:8]=[C:7]([C:12]([O:14]CC)=[O:13])[N:6]=1>C(O)C.O>[CH3:3][O:4][C:5]1[CH:10]=[C:9]([CH3:11])[N:8]=[C:7]([C:12]([OH:14])=[O:13])[N:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19778888HCID 19778888, compound

Product 1

HCID 197789074-Methoxy-6-methylpyrimidine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of 11.5 g of sodium hydroxide in 156 ml of ethanol and 78 ml of water is added to a stirred solution of 51.5 g of ethyl 4-methoxy-6methylpyrimidine-2-carboxylate in 280 ml of ethanol. Stirring is continued for 12 hours at room temperature, and the sodium salt of the carboxylic acid, which has precipitated, is filtered off with suction. The sodium salt is transferred to a solution of 17.3 g of acetyl chloride in 220 ml of methanol, and the sodium chloride, which has precipitated, is filtered off with suction. The methanolic solution is evaporated on a rotary evaporator. This gives 30.9 g of 4-methoxy-6-methylpyrimidine-2-carboxylic acid of melting point 140°-141° C. as the residue.

Workup

  1. customthe sodium salt of the carboxylic acid, which has precipitated
  2. filtrationis filtered off with suction
  3. customthe sodium chloride, which has precipitated
  4. filtrationis filtered off with suction
  5. customThe methanolic solution is evaporated on a rotary evaporator

Sources & evidence

ORD record
ord-60203c400f9f4d919c941eb22148d7d0
Source dataset
uspto-grants-1993_02
Patent number
US05186736

Reaction notes

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