Lithium hydroxide, monohydrate → 2-(4-Chloropyrimidin-5-yl)acetic acid

HRID 1888154Notes

Reaction equation

HRID 1888154 reaction equation
C([O:3][C:4](=[O:13])[CH2:5][C:6]1[C:7]([Cl:12])=[N:8][CH:9]=[N:10][CH:11]=1)C.O.[OH-].[Li+]>O.C(O)C>[Cl:12][C:7]1[C:6]([CH2:5][C:4]([OH:13])=[O:3])=[CH:11][N:10]=[CH:9][N:8]=1

Participants

5

Reactant 2

HCID 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 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 0.6 g (3 mmol) of ethyl(4-chloro-5-pyrimidinyl)acetate from Step A 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 N 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 N aqueous hydrogen chloride
  4. concentrationconcentrated in vacuo
  5. customto remove all volatiles

Sources & evidence

ORD record
ord-6102cdcae6fc4630bb7a6d1eb80c9587
Source dataset
uspto-grants-2013_08
Patent number
US08501786B2

Reaction notes

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