Tetrabutylammonium Fluoride → HCID 68181565, compound

HRID 1398702Notes

Reaction equation

HRID 1398702 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[C:12]3[CH:13]=[C:14]([C:17]#[C:18][C:19]4([OH:32])[CH2:22][CH:21]([C:23](C)(C)[O:24][SiH2]C(C)(C)C)[CH2:20]4)[CH:15]=[CH:16][C:11]=3[N:10]=[C:9]2[CH3:33])[N:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[C:12]3[CH:13]=[C:14]([C:17]#[C:18][C:19]4([OH:32])[CH2:22][CH:21]([CH2:23][OH:24])[CH2:20]4)[CH:15]=[CH:16][C:11]=3[N:10]=[C:9]2[CH3:33])[N:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131732116HCID 131732116, compound

Product 1

HCID 68181565HCID 68181565, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a solution of 1-[3-(4-amino-[1,3,5]triazin-2-yl)-2-methyl-3H-benzoimidazol-5-ylethynyl]-3-(tert-butyl-dimethyl-silanyloxymethyl)-cyclobutanol (55 mg, 0.1 mmol) in tetrahydrofuran (20 ml) was added tetrabutylammonium fluoride (70 mg, 0.3 mmol). Then the solution stirred overnight at room temperature. The reaction mixture was washed with water and purified by column to afford title compound (30 mg, 86%): 1H NMR (400 MHz, MeOD) delta 2.05-2.10 (m, 2H), 2.36-2.38 (m, 1H), 2.57-2.62 (m, 2H), 3.59 (d, J=6.4 Hz, 2H), 7.40 (dd, J=1.6, 8.0 Hz, 1H), 7.55 (dd, J=0.4, 8.4 Hz, 1H), 8.56 (dd, J=0.4, 1.6 Hz, 1H), 8.59 (s, 1H). LCMS: m/z=+351.1 (M+H)+.

Workup

  1. washThe reaction mixture was washed with water
  2. custompurified by column

Sources & evidence

ORD record
ord-4c88924111244fa2b9076483b802a195
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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