Methanol → HCID 67848961, compound

HRID 1109975Notes

Reaction equation

HRID 1109975 reaction equation
[Cl:1][C:2]1[C:3]([C:12]([O:14]C)=[O:13])=[N:4][C:5]([O:10][CH3:11])=[N:6][C:7]=1OC.[OH-:16].[Na+].[CH3:18]O>O>[Cl:1][C:2]1([O:16][CH3:18])[CH:7]=[N:6][C:5]([O:10][CH3:11])=[N:4][CH:3]1[C:12]([OH:14])=[O:13]

Participants

5

Reactant 3

HCID 887Methanol2×HCID 14798Sodium HydroxideHCID 19018491HCID 19018491, compound

Product 1

HCID 67848961HCID 67848961, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

29.5 g of methyl 5-chloro-2,6-dimethoxypyrimidine-4-carboxylate solid are added to a stirred solution of 5.4 g of sodium hydroxide in 100 ml of methanol and 5 ml of water. Stirring is continued at room temperature until completion of the hydrolysis (3H), methanol is distilled off and the residue is taken up in water. The aqueous phase is first extracted once using ethyl acetate, then acidified to pH 2-3 with conc. hydrochloric acid and extracted five times using dichloromethane. The combined dichloromethane extracts are dried over sodium sulfate, the solvent is distilled off and the residue is dried in vacuo at 50° c. 23.0 g of 5-chloro-2,5-dimethoxypyrimidine-4-carboxylic acid of melting point 117°-119° C. (dec.) are obtained in this way.

Workup

  1. distillationis distilled off
  2. extractionThe aqueous phase is first extracted once using ethyl acetate
  3. extractionextracted five times
  4. dry with materialThe combined dichloromethane extracts are dried over sodium sulfate
  5. distillationthe solvent is distilled off
  6. customthe residue is dried in vacuo at 50° c

Sources & evidence

ORD record
ord-1238e1afa37a4fe693fa4b16b36d7c65
Source dataset
uspto-grants-1994_06
Patent number
US05324710

Reaction notes

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