Methanol → HCID 19702872, compound

HRID 861332Notes

Reaction equation

HRID 861332 reaction equation
CO.C([O:5][C:6]([C:8]1[C:9]([C:14]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[O:15])=[N:10][CH:11]=[N:12][CH:13]=1)=[O:7])C.[OH-].[Na+]>O>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([C:14]([C:9]2[C:8]([C:6]([OH:7])=[O:5])=[CH:13][N:12]=[CH:11][N:10]=2)=[O:15])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 53833316HCID 53833316, compound

Product 1

HCID 19702872HCID 19702872, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a methanol solution(15 ml) of 4-(4-methoxyphenylcarbonyl)pyrimidine-5-carboxylic acid ethyl ester was added 4N NaOH(4 ml). The solution was stirred at room temperature for 15 h. Water was added to the reaction solution to dissolve the resulting solid. After removal of methanol the aqueous layer was washed with AcOEt, made pH2 with 2N HCl and extracted with AcOEt. The organic layer was washed with brine and dried over Na2SO4. After removal of the solvent the residue was recrystallized from AcOEt and hexane(1:1) to give 4-(4-methoxyphenylcarbonyl)pyrimidine-5-carboxylic acid(1.06 g) as a yellow solid.

Workup

  1. dissolutionto dissolve the resulting solid
  2. customAfter removal of methanol the aqueous layer
  3. washwas washed with AcOEt
  4. extractionextracted with AcOEt
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. customAfter removal of the solvent the residue
  8. customwas recrystallized from AcOEt and hexane(1:1)

Sources & evidence

ORD record
ord-f55b9fba3a58481ca6e7872e7ddd3209
Source dataset
uspto-grants-1998_02
Patent number
US05714479

Reaction notes

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