Tetrabutylammonium Fluoride → HCID 44208752, compound

HRID 1677365Notes

Reaction equation

HRID 1677365 reaction equation
[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=3)[N:15]=2)[N:10](COCC[Si](C)(C)C)[C:9]=1[CH3:37])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(OCC)C.O>[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=3)[N:15]=2)[NH:10][C:9]=1[CH3:37])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59540884HCID 59540884, compound

Product 1

HCID 44208752HCID 44208752, compoundYield 24.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 6-Methyl-2-(3,4,5-trimethoxy-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (64 mg) in 0.5 mL of THF was added 400 uL of 1.0 M TBAF in THF. Heated the mixture to 60° C. for 14 h. Diluted with diethyl ether and water and partitioned. The organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated. Flash purification (95:5 methylene chloride:Methanol) afforded 12 mg of 6-Methyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide as a yellow solid.

Workup

  1. custompartitioned
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customFlash purification (95:5 methylene chloride:Methanol)

Sources & evidence

ORD record
ord-077ba7b18afe41858ad30cc6d09fc1ca
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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