Ethanol → 2-(3-Fluorophenyl)pyrimidine-5-carboxylic acid

HRID 563866Notes

Reaction equation

HRID 563866 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[CH:12][C:11]([C:14]([O:16]C)=[O:15])=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.O1CCCC1.C(O)C>O>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[CH:10][C:11]([C:14]([OH:16])=[O:15])=[CH:12][N:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 8028TetrahydrofuranHCID 45073367HCID 45073367, compound

Product 1

HCID 450733632-(3-Fluorophenyl)pyrimidine-5-carboxylic acidYield 89.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of methyl 2-(3-fluorophenyl)pyrimidine-5-carboxylate (45 g, 0.19 ml) in a 1:1 mixture of tetrahydrofuran and ethanol (120 mL) was added Li(OH).H2O (12.2 g, 0.29 mol) dissolved in water (120 mL) and the reaction mixture was stirred at room temperature overnight. The reaction was concentrated under reduced pressure, dissolved in water (500 mL), acidified with 1N aqueous HCl and filtered. The residue was washed with water (100 mL×3) and dried to give 37 g (yield 89.5%) of 2-(3-fluorophenyl)pyrimidine-5-carboxylic acid. 1H NMR (DMSO-d6) 7.49 (m, 1H) 7.67 (m, 1H) 8.18 (m, 1H) 8.34 (m, 1H) 9.34 (s, 2H). LRMS (ES+) M+H 219.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. dissolutiondissolved in water (500 mL)
  3. filtrationfiltered
  4. washThe residue was washed with water (100 mL×3)
  5. customdried

Sources & evidence

ORD record
ord-7fdb16652e9a4b83b2e76518d24f0e66
Source dataset
uspto-grants-2011_11
Patent number
US08067589B2

Reaction notes

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