Sodium Bicarbonate → 4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzaldehyde

HRID 716031Notes

Reaction equation

HRID 716031 reaction equation
[OH:1][CH2:2][C:3]1[CH: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.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.C([O-])(O)=O.[Na+]>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])=[CH: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

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 710153161-(2-(4-(hydroxymethyl)phenylamino)-5-((2-(trimethylsilyl)ethoxy) methyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-oneHCID 178418287HCID 178418287, compound

Product 1

HCID 867121234-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzaldehydeYield 73.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

To a 100 ml three necked round bottom flask 1-(2-(4-(hydroxymethyl)phenylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-one (2.3 g, 0.0051 mole) was taken in CH2Cl2 (25 ml). The reaction mixture was cooled to 5° C. and PCC (4.84 g, 0.0225 mole) was added at the same temperature under nitrogen atmosphere. The reaction mixture was warmed up to RT and then stirred for 2 hr. After completion of the reaction, the reaction mixture was poured into saturated NaHCO3 solution (50 ml) under stifling at 10° C. and the aq. layer was extracted with CH2Cl2. The combined organic layer was dried over Na2SO4, filtered and concentrated to afford crude product which was purified using column purification by eluting the compound with 15-20% ethyl acetate in hexanes to yield 1.7 g of 4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzaldehyde.

Workup

  1. temperatureThe reaction mixture was warmed up to RT
  2. customAfter completion of the reaction
  3. customunder stifling at 10° C.
  4. extractionthe aq. layer was extracted with CH2Cl2
  5. dry with materialThe combined organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford crude product which
  9. customwas purified
  10. customcolumn purification
  11. washby eluting the compound with 15-20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-71dd95b6ac124c208aec7eb40bc311c2
Source dataset
uspto-grants-2015_11
Patent number
US09187487B2

Reaction notes

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