Hydrochloric Acid → 4-Ethylsulfanylpyrimidine-5-carboxylic acid

HRID 2201364Notes

Reaction equation

HRID 2201364 reaction equation
C([O:3][C:4]([C:6]1[C:7]([S:12][CH2:13][CH3:14])=[N:8][CH:9]=[N:10][CH:11]=1)=[O:5])C.[OH-].[K+].Cl>C1COCC1>[CH2:13]([S:12][C:7]1[C:6]([C:4]([OH:5])=[O:3])=[CH:11][N:10]=[CH:9][N:8]=1)[CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 117988910HCID 117988910, compound

Product 1

HCID 1179889234-Ethylsulfanylpyrimidine-5-carboxylic acidYield 90.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2.40 g of 4-ethylsulfanylpyrimidine-5-carboxylic acid ethyl ester, 12 ml of a 2 M aqueous potassium hydroxide solution and 8 ml of THF was stirred at room temperature for 1 hour. Concentrated hydrochloric acid was poured to the reaction mixture and neutralized, then the mixture was concentrated under reduced pressure, and THF was distilled. Concentrated hydrochloric acid was further added to the reaction mixture to adjust pH of the reaction mixture at 5, and the precipitated crystal was filtered. The resulting solid was washed with water and n-hexane and dried to obtain 1.89 g of 4-ethylsulfanylpyrimidine-5-carboxylic acid.

Workup

  1. concentrationneutralized, then the mixture was concentrated under reduced pressure, and THF
  2. distillationwas distilled
  3. additionConcentrated hydrochloric acid was further added to the reaction mixture
  4. filtrationthe precipitated crystal was filtered
  5. washThe resulting solid was washed with water and n-hexane
  6. customdried

Sources & evidence

ORD record
ord-295906b0cea345f2b006b61f7540ea59
Source dataset
uspto-grants-2016_06
Patent number
US09364000B2

Reaction notes

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