Tetrabutylammonium Fluoride → HCID 68181509, compound

HRID 1398703Notes

Reaction equation

HRID 1398703 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][CH:19]([CH:21]4[CH2:24][CH:23]([O:25][Si](C(C)(C)C)(C)C)[CH2:22]4)[OH:20])[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][CH:19]([CH:21]4[CH2:22][CH:23]([OH:25])[CH2:24]4)[OH:20])[CH:15]=[CH:16][C:11]=3[N:10]=[C:9]2[CH3:33])[N:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68181844HCID 68181844, compound

Product 1

HCID 68181509HCID 68181509, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a solution of 3-[3-(4-amino-[1,3,5]triazin-2-yl)-2-methyl-3H-benzoimidazol-5-yl]-1-[3-(tert-butyl-dimethyl-silanyloxy)-cyclobutyl]-prop-2-yn-1-ol (50 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 (20 mg, 57%): 1H NMR (400 MHz, MeOD) delta 1.80-2.20 (m, 3H), 2.32-2.43 (m, 2H), 2.94 (s, 3H), 3.56-3.70 (m, 0.5H), 4.05-4.17 (m, 0.5H), 4.45-4.48 (m, 0.5H), 7.35-7.51 (m, 2H), 8.53-8.57 (m, 2H). LCMS: m/z=+350.9 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-bcd48827f8a441c8890eab4652c3af9f
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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