Ethanol → 2-(4-Chloropyrimidin-5-yl)acetic acid

HRID 243689Notes

Reaction equation

HRID 243689 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][C:9]([O:11]CC)=[O:10])=[CH:6][N:5]=[CH:4][N:3]=1.C(O)C.O.[OH-].[Li+]>O>[Cl:1][C:2]1[C:7]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 168937Lithium hydroxide, monohydrateHCID 46856293Ethyl 2-(4-chloropyrimidin-5-YL)acetate

Product 1

HCID 229879302-(4-Chloropyrimidin-5-yl)acetic acidYield 83.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 0.6 g (3 mmol) of ethyl (4-chloro-5-pyrimidinyl)acetate from Step A above in 0.5 mL of water and 1.5 mL of ethanol was added 215 mg (5.11 mmol) of lithium hydroxide hydrate. The reaction mixture was stirred at ambient temperature for 2 h then concentrated in vacuo to remove all volatiles. The residue was diluted with 7 mL of 2.0 M aqueous hydrogen chloride and then concentrated in vacuo to remove all volatiles to yield the title compound (0.43 g, 83%). 1H-NMR (500 MHz, CD3OD) δ: 8.88 (s, 1H), 8.70 (s, 1H), 3.96 (s, 2H). LC-MS: m/z (E/S) 173 (MH)+.

Workup

  1. concentrationthen concentrated in vacuo
  2. customto remove all volatiles
  3. additionThe residue was diluted with 7 mL of 2.0 M aqueous hydrogen chloride
  4. concentrationconcentrated in vacuo
  5. customto remove all volatiles

Sources & evidence

ORD record
ord-e4679c803afb4b4e8689582fc25479b9
Source dataset
uspto-grants-2014_02
Patent number
US08653260B2

Reaction notes

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