[4,5-Dimethoxy-2-(1-methyl-2-phenyl-ethyl)-phenyl]-(2,4-dimethoxy-pyrimidin-5-yl)-methanol → [4,5-Dimethoxy-2-(1-methyl-2-phenyl-ethyl)-phenyl]-(2,4-dimethoxy-pyrimidin-5-yl)-methanone

HRID 1677239Notes

Reaction equation

HRID 1677239 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([CH:11]([C:13]2[C:14]([O:21][CH3:22])=[N:15][C:16]([O:19][CH3:20])=[N:17][CH:18]=2)[OH:12])=[C:5]([CH:23]([CH3:31])[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:4]=1>C1(C)C=CC=CC=1.O=[Mn]=O>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([C:11]([C:13]2[C:14]([O:21][CH3:22])=[N:15][C:16]([O:19][CH3:20])=[N:17][CH:18]=2)=[O:12])=[C:5]([CH:23]([CH3:31])[CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:4]=1

Participants

4

Reactant 1

HCID 59598559[4,5-Dimethoxy-2-(1-methyl-2-phenyl-ethyl)-phenyl]-(2,4-dimethoxy-pyrimidin-5-yl)-methanol

Product 1

HCID 59598600[4,5-Dimethoxy-2-(1-methyl-2-phenyl-ethyl)-phenyl]-(2,4-dimethoxy-pyrimidin-5-yl)-methanoneYield 67.9%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 1140TolueneSolvent

Procedure

To a solution of [4,5-dimethoxy-2-(1-methyl-2-phenyl-ethyl)-phenyl]-(2,4-dimethoxy-pyrimidin-5-yl)-methanol (0.418 g, 0.9 mmol) in 20 mL toluene was added MnO2 (0.335 g, 4.7 mmol). The mixture was warmed to reflux and H2O was removed via a Dean-Stark trap. After 1 hour the mixture was cooled, filtered through a pad of celite and concentrated in vacuo to give a crude oil. Purification via flash chromatography (7:3 hexane/ethyl acetate) afforded [4,5-dimethoxy-2-(1-methyl-2-phenyl-ethyl)-phenyl]-(2,4-dimethoxy-pyrimidin-5-yl)-methanone (0.258 g, 62%) as a clear oil.

Workup

  1. temperatureThe mixture was warmed
  2. temperatureto reflux
  3. customH2O was removed via a Dean-Stark trap
  4. temperatureAfter 1 hour the mixture was cooled
  5. filtrationfiltered through a pad of celite
  6. concentrationconcentrated in vacuo
  7. customto give a crude oil
  8. customPurification via flash chromatography (7:3 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3dd2bd8638fd43a4a1454aa7d1afd46b
Source dataset
uspto-grants-2011_08
Patent number
US08008313B2

Reaction notes

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