Triacetoxyperiodinane → HCID 57839040, compound

HRID 732953Notes

Reaction equation

HRID 732953 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14]([CH2:15][OH:16])=[C:13]([CH3:17])[N:12]=[C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:10]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14]([CH:15]=[O:16])=[C:13]([CH3:17])[N:12]=[C:11]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:10]=1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57839048HCID 57839048, compound

Product 1

HCID 57839040HCID 57839040, compoundYield 94.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (4-(2,4-dichlorophenyl)-6-methyl-2-phenylpyrimidin-5-yl)methanol (75 mg, 0.2 mmol) in CH2Cl2 (6 mL) was added Dess-Martin periodinane (102 mg, 0.24 mmol). The reaction was kept for 2 hrs and was diluted with EtOAc (10 mL). The organic layer was washed with saturated NaHCO3 solution (10 mL), and brine (10 mL), dried (MgSO4), filtered and concentrated under reduced pressure to give the crude product as a white solid (75 mg). The crude product was purified by flash chromatography (silica gel, 30% EtOAc/hexane) to give 4-(2,4-dichlorophenyl)-6-methyl-2-phenylpyrimidine-5-carbaldehyde (65 mg, 91% for 2 steps) as a white solid.

Workup

  1. washThe organic layer was washed with saturated NaHCO3 solution (10 mL), and brine (10 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto give the crude product as a white solid (75 mg)
  6. customThe crude product was purified by flash chromatography (silica gel, 30% EtOAc/hexane)

Sources & evidence

ORD record
ord-002b9aed08e14dc5a87628829a7fe404
Source dataset
uspto-grants-2009_09
Patent number
US07589088B2

Reaction notes

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