Triacetoxyperiodinane → 4-Chloro-2-phenylpyrimidine-5-carbaldehyde

HRID 732954Notes

Reaction equation

HRID 732954 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][N:5]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:3]=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[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:3]=1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 578390414-Chloro-2-phenyl-5-pyrimidinemethanol

Product 1

HCID 578390614-Chloro-2-phenylpyrimidine-5-carbaldehydeYield 85.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred (4-chloro-2-phenylpyrimidin-5-yl)methanol (242 mg, 1.10 mmol) in CH2Cl2 (11 mL) was added Dess-Martin periodinane (553 mg, 1.43 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 (250 mg). The crude product was purified by flash chromatography (silica gel, 20% EtOAc/hexane) to give 4-chloro-2-phenylpyrimidine-5-carbaldehyde (205 mg, 82% for 2 steps) as a white solid.

Workup

  1. washwas 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 (250 mg)
  6. customThe crude product was purified by flash chromatography (silica gel, 20% EtOAc/hexane)

Sources & evidence

ORD record
ord-fdd90f58403d43db8f38b7dff119b863
Source dataset
uspto-grants-2009_09
Patent number
US07589088B2

Reaction notes

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