Tetrabutylammonium Fluoride → HCID 58382014, compound

HRID 1628103Notes

Reaction equation

HRID 1628103 reaction equation
[Br:1][C:2]1[C:10]2[N:9]3[C:11]([CH3:24])=[N:12][C:13]([C:14]4[CH:19]=[CH:18][C:17]([C:20]([OH:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=4)=[C:8]3[CH:7]=[N:6][C:5]=2[N:4]([Si](C(C)C)(C(C)C)C(C)C)[CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Br:1][C:2]1[C:10]2[N:9]3[C:11]([CH3:24])=[N:12][C:13]([C:14]4[CH:15]=[CH:16][C:17]([C:20]([OH:23])([CH3:21])[CH3:22])=[CH:18][CH:19]=4)=[C:8]3[CH:7]=[N:6][C:5]=2[NH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58382028HCID 58382028, compound

Product 1

HCID 58382014HCID 58382014, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-(4-(8-bromo-1-methyl-6-(triisopropylsilyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)phenyl)propan-2-ol (0.300 g, 0.554 mmol; Preparation #AD.1) in THF (5 mL) was added TBAF (0.504 mL, 0.554 mmol). The mixture was stirred at about rt for about 1 h and then was partitioned between DCM (50 mL) and water (25 mL). The layers were separated and the aqueous phase was extracted with DCM (3×20 mL). The combined organic phases were washed with brine (100 mL) and then the solid was collected by filtration to give 2-(4-(8-bromo-1-methyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)phenyl)propan-2-ol (0.082 g, 39%). LC/MS (Table 2, Method a) Rt=1.87 min.; MS m/z: 387 (M+H)+. Syk IC50=A.

Workup

  1. customwas partitioned between DCM (50 mL) and water (25 mL)
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with DCM (3×20 mL)
  4. washThe combined organic phases were washed with brine (100 mL)
  5. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-bec021ad741b4700b6abf1f427d07c68
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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