Lithium Hydroxide → 2-(Methylthio)pyrimidine-5-carboxylic acid

HRID 2184226Notes

Reaction equation

HRID 2184226 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[CH:7][C:6]([C:9]([O:11]CC)=[O:10])=[CH:5][N:4]=1.[Li+].[OH-]>O1CCOCC1>[CH3:1][S:2][C:3]1[N:8]=[CH:7][C:6]([C:9]([OH:11])=[O:10])=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 10442716Ethyl 2-(methylthio)pyrimidine-5-carboxylate

Product 1

HCID 36317942-(Methylthio)pyrimidine-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1 Eq. of 2-methylthio-5-ethoxycarbonylpyrimidine were dissolved in dioxane and, after addition of 2 eq. of 2N LiOH, stirred overnight. The solvent was then removed under reduced pressure, and the residue was dissolved in EtOH. After addition of a stoichiometric amount of ethereal HCl, the solution was again evaporated to dryness. Water which was still present was removed by azeotropic drying with toluene once. (b) 2-Methylthio-5-hydroxymethylpyrimidine

Workup

  1. customThe solvent was then removed under reduced pressure
  2. dissolutionthe residue was dissolved in EtOH
  3. additionAfter addition of a stoichiometric amount of ethereal HCl
  4. customthe solution was again evaporated to dryness
  5. customWater which was still present was removed
  6. dry with materialby azeotropic drying with toluene once

Sources & evidence

ORD record
ord-a35e869f54494accbfc7339c91fba265
Source dataset
uspto-grants-2005_05
Patent number
US06900319B2

Reaction notes

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