Tetrabutylammonium Fluoride → HCID 68686088, compound

HRID 2238664Notes

Reaction equation

HRID 2238664 reaction equation
[Si]([O:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]([NH:27][C:28]2[N:33]=[C:32]([C:34]3[N:38]4[CH:39]=[CH:40][CH:41]=[C:42]([CH:43]([F:45])[F:44])[C:37]4=[N:36][CH:35]=3)[C:31]([C:46]#[N:47])=[CH:30][N:29]=2)[CH3:26])=[CH:21][CH:20]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[F:45][CH:43]([F:44])[C:42]1[C:37]2[N:38]([C:34]([C:32]3[C:31]([C:46]#[N:47])=[CH:30][N:29]=[C:28]([NH:27][CH:25]([C:22]4[CH:21]=[CH:20][C:19]([OH:18])=[CH:24][CH:23]=4)[CH3:26])[N:33]=3)=[CH:35][N:36]=2)[CH:39]=[CH:40][CH:41]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68686725HCID 68686725, compound

Product 1

HCID 68686088HCID 68686088, compoundYield 81.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

208 mg of the 2-{[1-(4-{[t-butyl(diphenyl)silyl]oxy}phenyl)ethyl]amino}-4-[8-(difluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidine-5-carbonitrile [111-1] was dissolved in 5 mL of tetrahydrofuran, then 320 μL of tetrabutylammonium fluoride (1.0M tetrahydrofuran solution) was added under an ice-cold condition, and stirred at room temperature for 1 hour. The reaction solution was diluted in 200 mL of ethyl acetate, and washed with phosphate buffer pH6.8 and saturated brine in the subsequent order. The obtained organic layer was dried over anhydrous magnesium sulfate, the insolubles were filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in a small amount of mixture solvent of chloroform and methanol (chloroform:methanol=9:1) and solidified by hexane, to obtain 107 mg of 4-[8-(difluoromethyl)imidazo[1,2-a]pyridin-3-yl]-2-{[1-(4-hydroxyphenyl)ethyl]amino}pyrimidine-5-carbonitrile [111-2] as a white solid.

Workup

  1. washwashed with phosphate buffer pH6.8 and saturated brine in the subsequent order
  2. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  3. filtrationthe insolubles were filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutionThe obtained residue was dissolved in a small amount of mixture solvent of chloroform and methanol (chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-54c2be5211c04bca958f8ac84d061307
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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