Lithium Hydroxide → HCID 68556656, compound

HRID 2381958Notes

Reaction equation

HRID 2381958 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([C:11](=[O:18])[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>[C:11]([C:8]1[N:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[CH:6][N:7]=1)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68554844HCID 68554844, compound

Product 1

HCID 68556656HCID 68556656, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-Benzoyl-pyrimidine-5-carboxylic acid methyl ester (420 mg, 1.73 mmol) is dissolved in THF (5 mL), and a solution of LiOH (46 mg, 1.91 mmol) in water (5 mL) is added in one portion at 0° C. The mixture is stirred at 0° C. for 60 min. THF is evaporated in vacuo, and the residue is diluted with water (5 mL) and washed with ether (10 mL). The aqueous layer is acidified with 2 N aqueous HCl to pH ˜3. The resulting precipitate is collected by filtration, washed with water three times, and dried in vacuum oven overnight to afford 2-benzoyl-pyrimidine-5-carboxylic acid (260 mg, 66%). MS: 229 (M+H); 1H NMR (300 MHz, DMSO): δ 7.60 (m, 3H), 7.73 (m, 1H), 7.85 (m, 2H), 9.4 (s, 1H).

Workup

  1. customTHF is evaporated in vacuo
  2. additionthe residue is diluted with water (5 mL)
  3. washwashed with ether (10 mL)
  4. filtrationThe resulting precipitate is collected by filtration
  5. washwashed with water three times
  6. customdried in vacuum oven overnight

Sources & evidence

ORD record
ord-9d48fdd375494db6aea2b3543342d1cc
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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