Citric Acid → HCID 21089196, compound

HRID 1713238Notes

Reaction equation

HRID 1713238 reaction equation
[F:1][C:2]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:3]=1[CH2:4][O:5][C:6]1[N:7]=[CH:8][N:9]([C:15]2[CH:16]=[C:17]([CH:22]=[CH:23][C:24]=2[CH3:25])[C:18]([O:20]C)=[O:19])[C:10](=[O:14])[C:11]=1[CH2:12][CH3:13].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCOCC1>[F:1][C:2]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:3]=1[CH2:4][O:5][C:6]1[N:7]=[CH:8][N:9]([C:15]2[CH:16]=[C:17]([CH:22]=[CH:23][C:24]=2[CH3:25])[C:18]([OH:20])=[O:19])[C:10](=[O:14])[C:11]=1[CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 21089019HCID 21089019, compound

Product 1

HCID 21089196HCID 21089196, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of methyl 3-[4-[(2,4-difluorobenzyl)oxy]-5-ethyl-6-oxopyrimidin-1(6H)-yl]-4-methylbenzoate (from Step 3) (0.58 g, 1.40 mmol) in dioxane (2 mL) was added 2N NaOH (1.05 mL, 2.10 mmol). Stirred at ambient temperature for 2 h. Cooled reaction mixture (0° C.), added 5% citric acid to precipitate the product, filtered solid, washed with water, and dried in vacuo. Obtained the product as a pale yellow solid (0.53 g, 95%). Used without further purification.

Workup

  1. temperatureCooled
  2. customreaction mixture (0° C.)
  3. customto precipitate the product
  4. filtrationfiltered solid
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-db4d686c8bc149a6a745be9d120e76d1
Source dataset
uspto-grants-2010_09
Patent number
US07795271B2

Reaction notes

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