Hydrochloric Acid → HCID 22674259, compound

HRID 1005972Notes

Reaction equation

HRID 1005972 reaction equation
C([O:3][C:4]([C:6]1[C:7]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=[O:5])C.[OH-].[Na+].Cl>C(O)C.O>[CH3:13][S:12][C:9]1[N:8]=[C:7]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])[C:6]([C:4]([OH:5])=[O:3])=[CH:11][N:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69925925HCID 69925925, compound

Product 1

HCID 22674259HCID 22674259, compoundYield 47.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 7.0 g (23.0 mmol) 2-methylsulfanyl-4-o-tolyloxy-pyrimidine-5-carboxylic acid ethyl ester in 50 ml ethanol a solution of 1.37 g (34.50 mmol) sodiumhydroxide in 30 ml water was added and the resulting mixture was stirred 1 h at RT. The pH of the solution was adjusted to 1 with 25% HCl. The mixture was extracted twice with CH2Cl2. The combined organic phases were dried (Na2SO4), filtered and evaporated. The resulting solid was triturated twice with 10 ml diisopropylether, filtered off and dried to give 3.00 g (47%) 2-methylsulfanyl-4-o-tolyloxy-pyrimidine-5-carboxylic acid as a colorless solid, MS (ISN): 257.1 (M-H)−.

Workup

  1. extractionThe mixture was extracted twice with CH2Cl2
  2. dry with materialThe combined organic phases were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe resulting solid was triturated twice with 10 ml diisopropylether
  6. filtrationfiltered off
  7. customdried

Sources & evidence

ORD record
ord-93d9da35638042dd8eccf0f2150c75e8
Source dataset
uspto-grants-2004_09
Patent number
US06787539B2

Reaction notes

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