Trifluoromethanesulfonic acid → HCID 21114627, compound

HRID 1817184Notes

Reaction equation

HRID 1817184 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5](Cl)=[N:6][CH:7]=1.[F:10][C:11]([F:17])([F:16])[CH2:12][CH2:13][CH2:14][OH:15].[F:18][C:19]([F:25])([F:24])S(O)(=O)=O>O>[Br:1][C:2]1[C:3]([O:15][CH2:14][CH2:13][CH2:12][C:19]([F:25])([F:24])[F:18])=[N:4][C:5]([O:15][CH2:14][CH2:13][CH2:12][C:11]([F:17])([F:16])[F:10])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 1363074,4,4-Trifluorobutan-1-olHCID 2899735-Bromo-2,4-dichloropyrimidine

Product 1

HCID 21114627HCID 21114627, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.19 g (14 mmol) of 5-bromo-2,4-dichloropyrimidine is mixed with 8.06 g (63 mmol) of 4,4,4-trifluorobutanol, and 0.74 ml (8.4 mmol) of trifluoromethanesulfonic acid is slowly added to it. The reaction mixture is stirred overnight at room temperature and then poured into water. The mixture is extracted by means of ethyl acetate, the combined organic phases are dried on MgSO2, and the solvent is evaporated by means of underpressure. The product is always contaminated with varying amounts of 2,4-bisalkoxypyrimidine. The remaining material is therefore purified by means of gradient chromatography with silica gel as a carrier medium (eluant: hexane and hexane/ethyl acetate at a 9:1 ratio). This process results in a yield of 1.70 g (38%) and also yields 1.93 g (34%) of 5-bromo-2,4-bis-(4,4,4-trifluorobutoxy)pyrimidine (starting compound).

Workup

  1. additionis slowly added to it
  2. extractionThe mixture is extracted by means of ethyl acetate
  3. customthe combined organic phases are dried on MgSO2
  4. customthe solvent is evaporated by means of underpressure
  5. customThe remaining material is therefore purified by means of gradient chromatography with silica gel as a carrier medium (eluant

Sources & evidence

ORD record
ord-ee9f363db63446baa8aaefafeb9de867
Source dataset
uspto-grants-2009_10
Patent number
US07598260B2

Reaction notes

Loading…