Trifluoromethanesulfonic acid → 5-[4-Fluoro-5-iodo-2-(1-methylethyl)phenoxy]-2,4-pyrimidinediamine

HRID 491491Notes

Reaction equation

HRID 491491 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[C:8]([NH2:14])=[N:9][C:10]([NH2:13])=[N:11][CH:12]=2)=[C:4]([CH:17]([CH3:19])[CH3:18])[CH:3]=1.FC(S(O)(=O)=O)(F)F.[I:28]N1C(=O)CCC1=O>C1COCC1>[F:1][C:2]1[C:16]([I:28])=[CH:15][C:5]([O:6][C:7]2[C:8]([NH2:14])=[N:9][C:10]([NH2:13])=[N:11][CH:12]=2)=[C:4]([CH:17]([CH3:19])[CH3:18])[CH:3]=1

Participants

5

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 120273N-IodosuccinimideHCID 57678409HCID 57678409, compound

Product 1

HCID 576784025-[4-Fluoro-5-iodo-2-(1-methylethyl)phenoxy]-2,4-pyrimidinediamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(4-Fluoro-2-isopropyl-phenoxy)-pyrimidine-2,4-diamine (400 mg, 1.53 mmol, prepared using the procedure of example 1) was dissolved in dry THF at ice bath temperature, and trifluoromethylsulfonic acid (0.67 mL, 7.63 mmol) was added. After stirring for 10 minutes, N-iodosuccinimide (378 g, 1.68 mmol) was added in portions. The ice bath was removed and the reaction mixture was stirred for three hours. The reaction mixture was then poured over ice and extracted with dichloromethane. The combined organic layers were washed with 10% aqueous sodium bisulfite solution and water, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was chromatographed on silica (95%:5%:1% CH2Cl2:MeOH:NH4OH) to give 338 mg of 5-(4-fluoro-5-iodo-2-isopropyl-phenoxy)-pyrimidine -2,4-diamine, MS (M+H)=389.

Workup

  1. additionwas added
  2. customThe ice bath was removed
  3. stirringthe reaction mixture was stirred for three hours
  4. additionThe reaction mixture was then poured over ice
  5. extractionextracted with dichloromethane
  6. washThe combined organic layers were washed with 10% aqueous sodium bisulfite solution and water
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was chromatographed on silica (95%:5%:1% CH2Cl2:MeOH:NH4OH)

Sources & evidence

ORD record
ord-a6ccc9eee65a49529ae4b55c343c15d3
Source dataset
uspto-grants-2009_05
Patent number
US07531547B2

Reaction notes

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