Lithium Hydroxide → HCID 68555610, compound

HRID 2381963Notes

Reaction equation

HRID 2381963 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:9][CH:10]=1)=[O:4].[Li+].[OH-]>C1COCC1.O>[O:11]([C:8]1[N:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:10][N:9]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68554907HCID 68554907, compound

Product 1

HCID 68555610HCID 68555610, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-phenoxy-pyrimidine-5-carboxylic acid methyl ester (0.5 g, 2.17 mmol) in THF (10 mL) and water (5 mL) is added LiOH (105 mg, 4.35 mmol). The reaction is stirred at 0° C. for 1 h. The THF is evaporated and the aqueous reissue is washed with ether, acidified with 2 M aqueous HCl. The resulting precipitate is filtered and dried to afford 2-phenoxy-pyrimidine-5-carboxylic acid (0.34 g, 73%) as a solid. MS: 217 (M+H); 1H NMR (300 MHz, CDCl3): δ 7.20-7.35 (m, 3H), 7.47 (t, 2H) 9.16 (s, 2H).

Workup

  1. customThe THF is evaporated
  2. washthe aqueous reissue is washed with ether
  3. filtrationThe resulting precipitate is filtered
  4. customdried

Sources & evidence

ORD record
ord-176070c27189492abb9899d576499eb6
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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