Hydrochloric Acid → HCID 22674283, compound

HRID 1005976Notes

Reaction equation

HRID 1005976 reaction equation
C([O:3][C:4]([C:6]1[C:7]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])=[N:8][C:9]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[N:10][CH:11]=1)=[O:5])C.[OH-].[Na+].Cl>C(O)C.O>[N:15]1[CH:16]=[CH:17][C:12]([C:9]2[N:8]=[C:7]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH3:25])[C:6]([C:4]([OH:5])=[O:3])=[CH:11][N:10]=2)=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69922894HCID 69922894, compound

Product 1

HCID 22674283HCID 22674283, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 0.70 g (2.08 mmol) 2-pyridin-4-yl-4-o-tolyloxy-pyrimidine-5-carboxylic acid ethyl ester in 20 ml ethanol a solution of 0.12 g (3.12 mmol) sodiumhydroxide in 10 ml water was added and the resulting mixture was stirred 2 h at RT. The pH of the solution was adjusted to 3 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 ethanol, filtered off and dried to give 0.60 g (94%) 2-pyridin-4-yl-4-o-tolyloxy-pyrimidine-5-carboxylic acid as a colorless solid, MS (EI): 307.1 (M+).

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 ethanol
  6. filtrationfiltered off
  7. customdried

Sources & evidence

ORD record
ord-4523af3530d54d41b39faba2d4c1d5da
Source dataset
uspto-grants-2004_09
Patent number
US06787539B2

Reaction notes

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