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

HRID 344584Notes

Reaction equation

HRID 344584 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-6-methylpyrimidine-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-8b8d473119454539ad6362f604bd4ea1
Source dataset
uspto-grants-1991_10
Patent number
US05053072

Reaction notes

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