Water → 2-Pyrimidinebutanal, 4-(trifluoromethyl)-

HRID 19665Notes

Reaction equation

HRID 19665 reaction equation
[CH2:1]([C:6]1[N:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][N:7]=1)[CH2:2][CH2:3][CH:4]=C.[OH2:16]>C1COCC1.O.O=[Os](=O)(=O)=O>[F:13][C:12]([F:15])([F:14])[C:10]1[CH:9]=[CH:8][N:7]=[C:6]([CH2:1][CH2:2][CH2:3][CH:4]=[O:16])[N:11]=1

Participants

5

Reactant 2

HCID 962WaterHCID 57856475Pyrimidine, 2-(4-penten-1-yl)-4-(trifluoromethyl)-

Product 1

HCID 219193682-Pyrimidinebutanal, 4-(trifluoromethyl)-

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 2-(4-penten-1-yl)-4-(trifluoromethyl)pyrimidine (P7, 143 mg) in THF/H2O 5/1 (6.5 mL) were added OsO4 (4% in water, 0.2 mL) and NaIO4 (424 mg). The solution was stirred at r.t. for 30 min. Water was then added and the mixture extracted with DCM. The organic phase was washed with brine, dried over Na2SO4, filtered and evaporated in vacuo to give 91 mg of the title compound as an oil, which was used in the subsequent step without further purification.

Workup

  1. extractionthe mixture extracted with DCM
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-e71696faeb264609a77adf5a3a35f374
Source dataset
uspto-grants-2010_06
Patent number
US07745458B2

Reaction notes

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