Trichloroisocyanuric Acid → 6-Chloro-2-phenylpyrimidine-4-carboxylic acid

HRID 1258365Notes

Reaction equation

HRID 1258365 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([CH2:14][OH:15])[CH:3]=1.C([O-])(O)=[O:17].[Na+].[Na+].[Br-].C1(N(Cl)C(=O)N(Cl)C(=O)N1Cl)=O>CC(C)=O.CC1(C)N([O])C(C)(C)CCC1>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([C:14]([OH:17])=[O:15])[CH:3]=1

Participants

7

Reactant 4

HCID 6909Trichloroisocyanuric AcidHCID 253881Sodium BromideHCID 516892Sodium BicarbonateHCID 53396316(6-Chloro-2-phenylpyrimidin-4-yl)methanol

Product 1

HCID 574316986-Chloro-2-phenylpyrimidine-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 2724126TempoCatalystHCID 180AcetoneSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of (6-chloro-2-phenyl-pyrimidin-4-yl)-methanol (240 g; prepared using a method analogous to the one described in WO 2006/114774, Example 24, intermediate 24.2) in acetone (2 L) was added an aq. NaHCO3 solution (15%, 961 mL). The mixture was cooled down to 5° C. and NaBr (11.2 g) followed by TEMPO (8.56 g) were added. TCCA (506 g) was then added portionwise over 1.5 h. The resulting mixture was stirred at RT for 1.5 h. The mixture was filtered through a pad of Celite and the solution was evaporated off. The residue was diluted in water/EA. The aq. phase was extracted with EA and the combined org. phases were dried (Na2SO4) and evaporated off. Recrystallization of the residue (EA/Hept) afforded the desired product as a beige solid (162.1 g).

Workup

  1. customprepared
  2. additionwere added
  3. filtrationThe mixture was filtered through a pad of Celite
  4. customthe solution was evaporated off
  5. additionThe residue was diluted in water/EA
  6. extractionThe aq. phase was extracted with EA
  7. dry with materialphases were dried (Na2SO4)
  8. customevaporated off
  9. customRecrystallization of the residue (EA/Hept)

Sources & evidence

ORD record
ord-b7ea497918924aa19b854d7fc8653f15
Source dataset
uspto-grants-2013_06
Patent number
US08466156B2

Reaction notes

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