tert-Butyl 3-((2-(methylthio)-5-(trifluoromethyl)pyrimidin-4-yl)ethynyl)benzoate → tert-Butyl 3-(2-(2-(methylthio)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)benzoate

HRID 1473031Notes

Reaction equation

HRID 1473031 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]#[C:10][C:11]2[CH:12]=[C:13]([CH:21]=[CH:22][CH:23]=2)[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:6]([C:24]([F:27])([F:26])[F:25])=[CH:5][N:4]=1>C1COCC1.[Pd]>[CH3:1][S:2][C:3]1[N:8]=[C:7]([CH2:9][CH2:10][C:11]2[CH:12]=[C:13]([CH:21]=[CH:22][CH:23]=2)[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:6]([C:24]([F:25])([F:26])[F:27])=[CH:5][N:4]=1

Participants

4

Reactant 1

HCID 71217514tert-Butyl 3-((2-(methylthio)-5-(trifluoromethyl)pyrimidin-4-yl)ethynyl)benzoate

Product 1

HCID 71209436tert-Butyl 3-(2-(2-(methylthio)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)benzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 3-((2-(methylthio)-5-(trifluoromethyl)pyrimidin-4-yl)ethynyl)benzoate (I18) (0.624 g, 1.58 mmol) and 10% Pd/C (0.206 g) was taken up in THF (20 mL) and H2 bubbled through the mixture for 5 minutes before stirring at room temperature for 20 hours under a hydrogen atmosphere. The mixture was filtered through celite and concentrated under reduced pressure. This procedure was repeated twice with 10% Pd/C (0.212 g) and 20% Pearlman's catalyst (0.316 g) respectively to give the title compound (I19) as a yellow oil that was reacted without further purification. LCMS Method C: rt 7.14 min.

Workup

  1. customH2 bubbled through the mixture for 5 minutes
  2. filtrationThe mixture was filtered through celite and
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0bae6c6f30a34c27a189b4805becf170
Source dataset
uspto-grants-2015_04
Patent number
US09012461B2

Reaction notes

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