Water → HCID 178524913, compound

HRID 2169201Notes

Reaction equation

HRID 2169201 reaction equation
C([O:5][C:6]([C:8]1[NH:9][C:10]([CH2:23][C:24]2[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:31])=[N:11][C:12](=[O:22])[C:13]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:7])(C)(C)C.[Li+].[OH-].O>O1CCCC1>[CH2:15]([O:14][C:13]1[C:12](=[O:22])[N:11]=[C:10]([CH2:23][C:24]2[C:25]([Cl:31])=[CH:26][CH:27]=[CH:28][C:29]=2[Cl:30])[NH:9][C:8]=1[C:6]([OH:7])=[O:5])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 178450869HCID 178450869, compound

Product 1

HCID 178524913HCID 178524913, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(Benzyloxy)-2-(2,6-dichlorobenzyl)-6-oxo-3,6-dihydro-pyrimidine-4-carboxylic acid tert-butyl ester (61) (0.24 g, 520 μmol, Eq: 1.00) and LiOH (62.3 mg, 2.6 mmol, Eq: 5) were stirred in tetrahydrofuran (2 ml)/water (1.00 ml) at reflux overnight. The solvent was mostly removed. The residue was taken up in water and was extracted once with ethyl acetate. The aqueous layer was acidified with HCl conc. The precipitate was collected by filtration, washed with water and dried to afford 5-benzyloxy-2-(2,6-dichlorobenzyl)-6-oxo-3,6-dihydro-pyrimidine-4-carboxylic acid (62) (0.202 g, 498 μmol, 95.8% yield) as a white solid.

Workup

  1. temperatureat reflux overnight
  2. customThe solvent was mostly removed
  3. extractionwas extracted once with ethyl acetate
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-0bd0c22926f340129ad0a84f9c4a70ef
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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