Lithium Hydroxide → HCID 59509047, compound

HRID 1020084Notes

Reaction equation

HRID 1020084 reaction equation
C([O:3][C:4](=[O:25])[CH2:5][N:6]([CH3:24])[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])[N:6]([CH2:5][C:4]([OH:25])=[O:3])[CH3:24])[CH:15]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59509041HCID 59509041, compound

Product 1

HCID 59509047HCID 59509047, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {3-[6-(2-methoxy-phenyl)-pyrimidin-4-yl]-1-methyl-ureido}-acetic acid ethyl ester (LVIII) (370 mg, 1.03 mmol) in a mixture of THF and water (1:1) was added a solution of LiOH (87.0 mg, 2.06 mmol) in water at ice bath temperature over 10 min and then allowed to stir for two hours at room temperature. 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 combined organic phases were washed with water and brine, dried over anhydrous sodium sulfate and concentrated in a vacuum rotavapor to give {3-[6-(2-methoxy-phenyl)-pyrimidin-4-yl]-1-methyl-ureido}-acetic acid as a brown coloured solid. Yield: 34 mg, 10.4%.

Workup

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

Sources & evidence

ORD record
ord-826192a5a5fb4f4ca9c10c25161d6740
Source dataset
uspto-grants-2014_05
Patent number
US08716296B2

Reaction notes

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