Triacetoxyperiodinane → 5-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)picolinaldehyde

HRID 716048Notes

Reaction equation

HRID 716048 reaction equation
[OH:1][CH2:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10]2[N:11]=[C:12]3[C:18]([C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:17][N:16]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:13]3=[N:14][CH:15]=2)=[CH:5][CH:4]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:19]([C:18]1[C:12]2[C:13](=[N:14][CH:15]=[C:10]([NH:9][C:6]3[CH:5]=[CH:4][C:3]([CH:2]=[O:1])=[N:8][CH:7]=3)[N:11]=2)[N:16]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:30])([CH3:32])[CH3:31])[CH:17]=1)(=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 710153681-(2-(6-(hydroxymethyl)pyridin-3-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-one

Product 1

HCID 867121295-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)picolinaldehydeYield 54.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 100 ml three necked round bottom flask, 1-(2-(6-(hydroxymethyl)pyridin-3-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-one (0.32 g, 0.000702 mole) was taken in CH2Cl2 (20 ml) and cooled to 0° C. Dess Martin's reagent (1.11 g, 0.00245 mole) was added at 0° C. and the reaction was warmed to room temperature and stirred for 2 hrs under nitrogen atmosphere. After completion of the reaction, the reaction mixture was filtered through celite bed and washed with CH2Cl2. Filtrate was washed with water. Organic layers were combined, dried over Na2SO4, filtered and concentrated to afford crude product which was purified using column purification by eluting with 25-30% ethyl acetate in hexanes to yield 0.173 g of 5-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-2-yl-amino)-picolinaldehyde.

Workup

  1. temperaturethe reaction was warmed to room temperature
  2. customAfter completion of the reaction
  3. filtrationthe reaction mixture was filtered through celite bed
  4. washwashed with CH2Cl2
  5. washFiltrate was washed with water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford crude product which
  10. customwas purified
  11. customcolumn purification
  12. washby eluting with 25-30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-370d89b23031425d80869724630f3de2
Source dataset
uspto-grants-2015_11
Patent number
US09187487B2

Reaction notes

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