Selenium Dioxide → (S)-Methyl 2-(4-formyl-6-methylpyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropanoate

HRID 1513205Notes

Reaction equation

HRID 1513205 reaction equation
[Se](=O)=[O:2].[CH3:4][C:5]1[CH:10]=[C:9]([CH3:11])[N:8]=[C:7]([O:12][C@@H:13]([C:18]([O:31][CH3:32])([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:14]([O:16][CH3:17])=[O:15])[N:6]=1>O1CCOCC1.O.CCOCC>[CH:11]([C:9]1[CH:10]=[C:5]([CH3:4])[N:6]=[C:7]([O:12][C@@H:13]([C:18]([O:31][CH3:32])([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:14]([O:16][CH3:17])=[O:15])[N:8]=1)=[O:2]

Participants

6

Reactant 2

HCID 24007Selenium Dioxide2×HCID 46244104(S)-Methyl 2-((4,6-dimethylpyrimidin-2-yl)oxy)-3-methoxy-3,3-diphenylpropanoate

Product 1

HCID 59441456(S)-Methyl 2-(4-formyl-6-methylpyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropanoate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

Selenium dioxide (8.5 g, 76 mmol) is dissolved in a solution of dioxane (238 mL) and water (40 mL) at 55-60° C. To the solution of selenium dioxide, the compound of Example 9 (20 g, 51 mmol) is added and then the reaction mixture is heated at reflux for 10 hr. The reaction mixture is cooled to room temperature, diluted with ether (200 mL) and filtered. The filtrate is concentrated at reduced pressure on a rotary evaporator and then extracted with ethyl acetate (2×100 mL) to yield the crude title compound. MS m/z 406.9 (M+.+1).

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux for 10 hr
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated at reduced pressure on a rotary evaporator
  5. extractionextracted with ethyl acetate (2×100 mL)

Sources & evidence

ORD record
ord-0d928537abaa4b629be709b954de6295
Source dataset
uspto-grants-2012_07
Patent number
US08217155B2

Reaction notes

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