Lithium Hydroxide → HCID 59508985, compound

HRID 1020081Notes

Reaction equation

HRID 1020081 reaction equation
C([O:3][C:4](=[O:24])[CH2:5][NH:6][C:7]([NH:9][C:10]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])[N:13]=[CH:12][N:11]=1)=[O:8])C.[Li+].[OH-]>C1COCC1.O>[CH3:23][O:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:14]1[N:13]=[CH:12][N:11]=[C:10]([NH:9][C:7](=[O:8])[NH:6][CH2:5][C:4]([OH:24])=[O:3])[CH:15]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59509129HCID 59509129, compound

Product 1

HCID 59508985HCID 59508985, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {3-[6-(2-methoxy-phenyl)-pyrimidin-4-yl]-ureido}-acetic acid ethyl ester (LII) (190 mg, 0.57 mmol) in a mixture of THF and water (1:1) was added LiOH (50.0 mg, 1.12 mmol) solution in water at ice bath temperature over 10 min and the mixture was then allowed to stir for 2 hours. THF was evaporated and the aqueous solution was acidified with 2N HCl. This aqueous phase was then extracted with ethyl acetate (2×100 ml). The organic phases were separated, combined, washed with water and brine, dried over anhydrous sodium sulfate and concentrated in a vacuum rotavapor to afford {3-[6-(2-methoxy-phenyl)-pyrimidin-4-yl]-ureido}-acetic acid as a white solid. Yield: 184 mg, ˜quantitative.

Workup

  1. customTHF was evaporated
  2. extractionThis aqueous phase was then extracted with ethyl acetate (2×100 ml)
  3. customThe organic phases were separated
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in a vacuum rotavapor

Sources & evidence

ORD record
ord-a2600ccd3648442f9230aa73ca9ef522
Source dataset
uspto-grants-2014_05
Patent number
US08716296B2

Reaction notes

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