HCID 57584033, compound → HCID 57584006, compound

HRID 910611Notes

Reaction equation

HRID 910611 reaction equation
COC1C=CC(C[N:8]2[C:13](=[O:14])[C:12]([C:15]3[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=3)=[CH:11][N:10]=[CH:9]2)=CC=1>FC(F)(F)C(O)=O>[O:14]=[C:13]1[NH:8][CH:9]=[N:10][CH:11]=[C:12]1[C:15]1[CH:16]=[CH:17][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:23][CH:24]=1

Participants

3

Reactant 1

HCID 57584033HCID 57584033, compound

Product 1

HCID 57584006HCID 57584006, compoundYield 63.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
70 °C

Procedure

Methyl 4-[1-(4-methoxybenzyl)-6-oxo-1,6-dihydropyrimidin-5-yl]benzoate (205 mg) was dissolved in trifluoroacetic acid (5 mL), followed by stirring at 70° C. for 15 hours. The reaction mixture was evaporated under reduced pressure, followed by two times azeotropy with toluene. Water was added to the resulting residue, followed by three times extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate, then the solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (methanol/chloroform=2% to 5%) to obtain methyl 4-(6-oxo-1,6-dihydropyrimidin-5-yl)benzoate (86 mg) as a white solid.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. additionWater was added to the resulting residue
  3. extractionfollowed by three times extraction with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. customthe resulting residue was purified by silica gel column chromatography (methanol/chloroform=2% to 5%)

Sources & evidence

ORD record
ord-e93edad14f0f4cc8b7fd8321c7225034
Source dataset
uspto-grants-2011_09
Patent number
US08022208B2

Reaction notes

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