Triacetoxyperiodinane → HCID 86695074, compound

HRID 574348Notes

Reaction equation

HRID 574348 reaction equation
[C:1]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:30]=[C:10]3[N:11]=[C:12]([CH3:29])[C:13]([CH:23]([OH:28])[C:24]([O:26][CH3:27])=[O:25])=[C:14]([N:15]4[CH2:20][CH2:19][C:18]([CH3:22])([CH3:21])[CH2:17][CH2:16]4)[N:9]3[N:8]=2)[CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>C(Cl)Cl>[C:1]1([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:30]=[C:10]3[N:11]=[C:12]([CH3:29])[C:13]([C:23](=[O:28])[C:24]([O:26][CH3:27])=[O:25])=[C:14]([N:15]4[CH2:16][CH2:17][C:18]([CH3:22])([CH3:21])[CH2:19][CH2:20]4)[N:9]3[N:8]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86695075HCID 86695075, compound

Product 1

HCID 86695074HCID 86695074, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a soln. of methyl 2-(2-([1,1′-biphenyl]-3-yl)-7-(4,4-dimethylpiperidin-1-yl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)-2-hydroxyacetate (73 mg, 0.150 mmol) in CH2Cl2 (5 mL) was added Dess-MartinPeriodinane (70.1 mg, 0.165 mmol) and the resulting mixture was stirred at room temp for 1 hr and then diluted with ethyl 5 mL) and washed with sat. NaHCO3 solution (5 mL), dried (Na2SO4), filtered and concentrated and purified by Biotage (90 g, eluted from 3-32% EtOAc/Hexane) to afford methyl 2-(2-([1,1′-biphenyl]-3-yl)-7-(4,4-dimethylpiperidin-1-yl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)-2-oxoacetate (61 mg, 0.124 mmol, 82% yield).

Workup

  1. additiondiluted with ethyl 5 mL) and
  2. washwashed with sat. NaHCO3 solution (5 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by Biotage (90 g, eluted from 3-32% EtOAc/Hexane)

Sources & evidence

ORD record
ord-35090ee7084f4fffbd1dd3b86d82a6db
Source dataset
uspto-grants-2015_05
Patent number
US09034882B2

Reaction notes

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