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

HRID 1947725Notes

Reaction equation

HRID 1947725 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH:9]([CH3:14])[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]([CH:9]([CH3:14])[C:10]([OH:12])=[O:11])=[CH:7][N:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 168937Lithium hydroxide, monohydrateHCID 57907415Methyl 2-(4-methoxypyrimidin-5-yl)propanoate

Product 1

HCID 579074022-(4-Methoxypyrimidin-5-yl)propanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 0.21 g (1.06 mmol) of methyl 2-(4-methoxypyrimidin-5-yl)propanoate from Step B 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 N aqueous hydrogen chloride and then concentrated in vacuo to remove all volatiles to yield the title compound as an off white solid (70 mg, 36%). 1H-NMR (500 MHz, CD3OD) δ: 8.67 (s 1H), 8.4 (s, 1H), 4.07 (s, 3H), 3.9 (q, J=7 Hz, 2H), 1.58 (d, J=7 Hz, 3H). LC-MS: m/z (E/S) 183 (MH)+.

Workup

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

Sources & evidence

ORD record
ord-dc9f9bd5f0d44d80887d871b5fcfb0c3
Source dataset
uspto-grants-2013_03
Patent number
US08399480B2

Reaction notes

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