Water → 4-(4-Phenyl-2-pyrimidinyl)butanal

HRID 19663Notes

Reaction equation

HRID 19663 reaction equation
[CH2:1]([C:6]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:9]=[CH:8][N:7]=1)[CH2:2][CH2:3][CH:4]=C.[OH2:18]>C1COCC1.O.O=[Os](=O)(=O)=O>[C:12]1([C:10]2[CH:9]=[CH:8][N:7]=[C:6]([CH2:1][CH2:2][CH2:3][CH:4]=[O:18])[N:11]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 962WaterHCID 578564872-(4-Penten-1-yl)-4-phenylpyrimidine

Product 1

HCID 578564634-(4-Phenyl-2-pyrimidinyl)butanal

Reagents, catalysts & solvents 2

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

Procedure

To a stirred solution of 2-(4-penten-1-yl)-4-phenylpyrimidine (P5, 142 mg) in THF/H2O (5/1 mL) were added OsO4 (4% in water, 0.2 mL) and NaIO4 (404 mg). The solution was stirred at room temperature for 0.5 h. 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 141 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-23699602754a4235bc24b972126b8826
Source dataset
uspto-grants-2010_06
Patent number
US07745458B2

Reaction notes

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