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

HRID 1947722Notes

Reaction equation

HRID 1947722 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9][C:10]([O:12]C)=[O:11])=[CH:7][N:6]=[CH:5][N:4]=1.C(O)C.O.[OH-].[Li+]>O>[CH3:1][O:2][C:3]1[C:8]([CH2:9][C:10]([OH:12])=[O:11])=[CH:7][N:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 168937Lithium hydroxide, monohydrateHCID 57907464Methyl(4-methoxy-5-pyrimidinyl)acetate

Product 1

HCID 579075382-(4-Methoxypyrimidin-5-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 0.21 g (1.14 mmol) of methyl (4-methoxy-5-pyrimidinyl)acetate from Step A above in 0.5 mL of water and 1.5 mL of ethanol was added 81 mg (1.9 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 3 mL of 2.0 M aqueous hydrogen chloride and then concentrated in vacuo to remove all volatiles to yield the title compound as an off white solid (191 mg, 90%). 1H-NMR (500 MHz, CD3OD) δ: 8.72 (s, 1H), 8.35 (s, 1H), 4.01 (s, 3H), 3.57 (s, 2H). LC-MS: m/z (E/S) 169 (MH)+.

Workup

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

Sources & evidence

ORD record
ord-015f84feb4f24f6fb3fe74434cfb7ff1
Source dataset
uspto-grants-2013_03
Patent number
US08399480B2

Reaction notes

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