Trifluoroacetic acid → HCID 59837993, compound

HRID 272636Notes

Reaction equation

HRID 272636 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].[Cl:5][C:6]1[N:11]=[C:10](Cl)[C:9]([C:13]([F:16])([F:15])[F:14])=[CH:8][N:7]=1.FC(F)(F)C(O)=O>>[Cl:5][C:6]1[N:11]=[C:10]([O:4][CH2:1][C:2]#[CH:3])[C:9]([C:13]([F:16])([F:15])[F:14])=[CH:8][N:7]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7859Propargyl alcoholHCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidine

Product 1

HCID 59837993HCID 59837993, compound

Conditions

Temperature
0 °C

Procedure

3.97 ml (68.2 mmol) Prop-2-yn-1-ol are slowly added to 3.40 g (15.6 mmol) of 2,4-Dichloro-5-trifluoromethyl-pyrimidine at 0° C. under a nitrogen atmosphere. 0.79 ml Trifluoro-acetic acid are added dropwise and the batch is stirred for 6 hours at 0° C. The batch is poured on ice and extracted with ethyl acetate (3×). The combined organic phases are washed with water, dried (Na2SO4), filtered and concentrated by evaporation. The remaining residue is purified by chromatography (hexane/ethyl acetate 95:5). 591 mg (2.5 mmol, corresponding to 16% of theory) of the product is obtained.

Workup

  1. additionThe batch is poured on ice
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined organic phases are washed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. customThe remaining residue is purified by chromatography (hexane/ethyl acetate 95:5)
  8. custom591 mg (2.5 mmol, corresponding to 16% of theory) of the product is obtained

Sources & evidence

ORD record
ord-3cdb3d4465db4b8b9a2caf4f80f7592c
Source dataset
uspto-grants-2008_11
Patent number
US07456191B2

Reaction notes

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