Lithium Hydroxide → HCID 67044166, compound

HRID 1944450Notes

Reaction equation

HRID 1944450 reaction equation
C[O:2][C:3]([C:5]1[C:10]([S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:9][N:8]=[C:7]([S:20][CH3:21])[N:6]=1)=[O:4].[OH-].[Li+]>O1CCCC1>[C:14]1([S:11]([C:10]2[C:5]([C:3]([OH:4])=[O:2])=[N:6][C:7]([S:20][CH3:21])=[N:8][CH:9]=2)(=[O:13])=[O:12])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 670443825-Benzenesulfonyl-2-methylsulfanylpyrimidine-4-carboxylic acid methyl ester

Product 1

HCID 67044166HCID 67044166, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-benzenesulfonyl-2-methylsulfanylpyrimidine-4-carboxylic acid methyl ester (1.4 g) and tetrahydrofuran (20 mL) was treated with 1.0 M aqueous lithium hydroxide solution (2.2 mL), and the resulting mixture was stirred at room temperature for 1 hour. The mixture was concentrated under reduced pressure, pH adjusted to 4 by the addition of 0.1 M aqueous hydrochloric acid solution and extracted with ethyl acetate. The combined extract was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure to afford the title compound as a pale yellow solid (1.3 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionpH adjusted to 4 by the addition of 0.1 M aqueous hydrochloric acid solution
  3. extractionextracted with ethyl acetate
  4. extractionThe combined extract
  5. washwas washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7019f26e81cf48d09b85f4aab9758ea4
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

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