Lithium Hydroxide → (4R)-4-(3,4-difluorophenyl)-6-(methoxymethyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylic acid

HRID 2085438Notes

Reaction equation

HRID 2085438 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[C:14]([C:15]([O:17]C)=[O:16])=[C:13]([CH2:19][O:20][CH3:21])[NH:12][C:11](=[O:22])[NH:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[OH-].[Li+]>O.C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[C:14]([C:15]([OH:17])=[O:16])=[C:13]([CH2:19][O:20][CH3:21])[NH:12][C:11](=[O:22])[NH:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 54490798methyl (4R)-4-(3,4-difluorophenyl)-6-(methoxymethyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate

Product 1

HCID 10780384(4R)-4-(3,4-difluorophenyl)-6-(methoxymethyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylic acidYield 90%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A stirred mixture of one mole equivalent of methyl (4R)-4-(3,4-difluorophenyl)-6-(methoxymethyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate (10.0 g, 32.0 mmol) and lithium hydroxide (2 equivalents, 1.53 g, 64.0 mol) in H2O-THF (2:1, 300 mL) was heated at reflux temperature for 1 h. The reaction mixture was concentrated, dissolved in water, washed with ethyl acetate and acidified (1 N HCl) to pH 3-4 (pH paper). The precipitated product was collected, washed with water and dried under reduced pressure to give the desired product in 90% yield.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 1 h
  3. concentrationThe reaction mixture was concentrated
  4. dissolutiondissolved in water
  5. washwashed with ethyl acetate
  6. customThe precipitated product was collected
  7. washwashed with water
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-902e2ae6cc804dcd99c6471f915dba3a
Source dataset
uspto-grants-2004_04
Patent number
US06720324B2

Reaction notes

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