Sodium Hydroxide → 4-(2,5-Dichloro-phenoxy)-pyrimidine-5-carboxylic acid

HRID 1025903Notes

Reaction equation

HRID 1025903 reaction equation
C([O:3][C:4]([C:6]1[C:7]([O:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[Cl:20])=[N:8][CH:9]=[N:10][CH:11]=1)=[O:5])C.[OH-].[Na+]>O1CCCC1.O>[Cl:20][C:14]1[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:13]=1[O:12][C:7]1[C:6]([C:4]([OH:5])=[O:3])=[CH:11][N:10]=[CH:9][N:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67320100HCID 67320100, compound

Product 1

HCID 673202614-(2,5-Dichloro-phenoxy)-pyrimidine-5-carboxylic acidYield 82.3%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

To a solution of 515 mg (1.64 mmol) 4-(2,5-dichloro-phenoxy)-pyrimidine-5-carboxylic acid ethyl ester in 10 mL tetrahydrofuran/water (2/1 v/v) was added 3.29 mL (3.28 mmol) 1M aqueous sodium hydroxide solution and the resulting solution was heated by microwave irradiation (Emrys Optimizer, Personal Chemistry) 30 minutes at 80° C. Solvents were evaporated under vacuum and the residue extracted three times with ethyl acetate and 1M aqueous hydrochloric acid. The combined organic layers were dried over magnesium sulfate, filtered and evaporated to give 385 mg (57%) of the desired compound as an off-white powder. MS (ESI): m/z=238.8 [M−H]−.

Workup

  1. customSolvents were evaporated under vacuum
  2. extractionthe residue extracted three times with ethyl acetate and 1M aqueous hydrochloric acid
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-08309a68b10243c58d569b1ce4e66e3a
Source dataset
uspto-grants-2014_05
Patent number
US08729091B2

Reaction notes

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