Tetrahydrofuran → 2,4-Dichloro-5-pyrimidinecarboxylic acid

HRID 645509

Reaction equation

HRID 645509 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9](Cl)=[O:10])=[CH:4][N:3]=1.C1C[O:15]CC1>O>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]([OH:10])=[O:15])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 137841122,4-Dichloropyrimidine-5-carbonyl chloride

Product 1

HCID 219418962,4-Dichloro-5-pyrimidinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of the 2,4-dichloropyrimidine-5-carbonyl chloride (24 mmol) in THF (24 mL) is added H2O (0.64 mL) at room temperature. The reaction mixture is stirred at room temperature for 0.83 h and then diluted with H2O. The mixture is extracted with AcOEt. The organic extracts are washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give the crude titled compound; 1H NMR (CDCl3) δ 6.80 (brs, 1H), 9.18 (s, 1H).

Workup

  1. extractionThe mixture is extracted with AcOEt
  2. washThe organic extracts are washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a6d60d2669694752a24f9d7362b9c7a5
Source dataset
uspto-grants-2010_04
Patent number
US07704996B2

Linked notes

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