Water → HCID 178524912, compound

HRID 2169207Notes

Reaction equation

HRID 2169207 reaction equation
C([O:5][C:6]([C:8]1[NH:9][C:10]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Br:30])=[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[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Br: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 178450868HCID 178450868, compound

Product 1

HCID 178524912HCID 178524912, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(Benzyloxy)-2-(2-bromobenzyl)-6-oxo-3,6-dihydro-pyrimidine-4-carboxylic acid tert-butyl ester (67) (2.69 g, 5.71 mmol, Eq: 1.00) and LiOH (683 mg, 28.5 mmol, Eq: 5) were stirred in tetrahydrofuran (18 ml)/water (9.00 ml) under reflux for 6 h, at room temperature overnight and again to reflux for 3 h. Then the solvent was mostly removed. The remaining oil was diluted with water and extracted with ethyl acetate. The aqueous layer was cooled in an ice bath and was acidified with HCl conc. Precipitate formed, was collected by filtration, washed with water and dried to afford 5-(benzyloxy)-2-(2-bromobenzyl)-6-oxo-3,6-dihydro-pyrimidine-4-carboxylic acid (68) (2.14 g, 5.15 mmol, 90.3% yield) as a white solid.

Workup

  1. temperatureagain to reflux for 3 h
  2. customThen the solvent was mostly removed
  3. additionThe remaining oil was diluted with water
  4. extractionextracted with ethyl acetate
  5. temperatureThe aqueous layer was cooled in an ice bath
  6. customformed
  7. filtrationwas collected by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-98aa5b95e67f46898c0d883550957e35
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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