Potassium Hydroxide → HCID 57831039, compound

HRID 600380Notes

Reaction equation

HRID 600380 reaction equation
Br[C:2]1[N:3]=[C:4]2[C:10]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:5]2=[N:6][CH:7]=1.[O:25]1CCOCC1.C(P(C(C)(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C.[OH-].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH3:13][C:12]([CH3:15])([CH3:14])[C:11]([C:10]1[C:4]2[NH:3][C:2](=[O:25])[CH:7]=[N:6][C:5]=2[N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH:9]=1)=[O:16]

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 312751,4-DioxaneHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneHCID 578292211-(2-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-yl)-2,2-dimethylpropane-1-one

Product 1

HCID 57831039HCID 57831039, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-[2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (0.067 g, 0.16 mmol), 0.4 mL dioxane, 0.4 mL water, Pd2(dba)3 (0.009 g, 0.01 mmol), 2-di-t-butylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl (0.008 g, 0.02 mmol), and freshly ground KOH (0.038 g, 0.67 mmol) in a sealed tube under N2 was stirred at 100° C. for 15 h. The resulting orange-black mixture was partitioned between 5 mL of ethyl acetate and 5 mL of water, with a few drops of ethanol added to reduce emulsions. The aqueous layer was extracted with 5 mL of ethyl acetate. The combined organic layers were dried over Na2SO4, filtered, and concentrated to an orange oil. Silica gel chromatography (20→40% EtOAc/hexanes) afforded 0.029 g (51%) of 7-(2,2-dimethyl-propionyl)-5-(2-trimethylsilanyl-ethoxymethyl)-1,5-dihydro-pyrrolo[2,3-b]pyrazin-2-one as a pale yellow solid.

Workup

  1. customThe resulting orange-black mixture was partitioned between 5 mL of ethyl acetate and 5 mL of water, with a few drops of ethanol
  2. additionadded
  3. extractionThe aqueous layer was extracted with 5 mL of ethyl acetate
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to an orange oil

Sources & evidence

ORD record
ord-dbaa3d613d2647db9a19e8069152da56
Source dataset
uspto-grants-2011_03
Patent number
US07902197B2

Reaction notes

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