Hydrochloric Acid → HCID 23512576, compound

HRID 354001Notes

Reaction equation

HRID 354001 reaction equation
C([O:3][C:4]([C:6]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])=[CH:10][N:9]=[C:8]([S:19][CH3:20])[N:7]=1)=[O:5])C.[OH-].[Na+].Cl>C(O)C>[Cl:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:11]1[C:6]([C:4]([OH:5])=[O:3])=[N:7][C:8]([S:19][CH3:20])=[N:9][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11243788HCID 11243788, compound

Product 1

HCID 23512576HCID 23512576, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3.00 g (9.72 mmol) 5-(2-chloro-phenyl)-2-methylsulfanyl-pyrimidine-4-carboxylic acid ethyl ester in 15 ml ethanol a solution of 0.58 g (14.5 mmol) NaOH in 15 ml was added at RT and the reaction solution was stirred for 1 hr. The pH of the solution was than adjusted to 1 by addition of 25% HCl. The resulting solution was extracted twice with 100 ml CH2Cl2/methanol (2:1). The combined organic phases were dried (MgSO4), filtered and evaporated. The residue was suspended in 20 ml diisopropylether, filtered and dried to give 2.40 g (88%) 5-(2-chloro-phenyl)-2-methylsulfanyl-pyrimidine-4-carboxylic acid as an off-white solid.

Workup

  1. extractionThe resulting solution was extracted twice with 100 ml CH2Cl2/methanol (2:1)
  2. dry with materialThe combined organic phases were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-64b61b2953f7493db185a8310c8d2abf
Source dataset
uspto-grants-2004_06
Patent number
US06756380B1

Reaction notes

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