Tetrabutylammonium Fluoride → 4-[3-(4-amino-[1,3,5]triazin-2-yl)-2-methyl-3H-benzoimidazol-5-yl]-2,2-dimethyl-but-3-yn-1-ol

HRID 1398705Notes

Reaction equation

HRID 1398705 reaction equation
C([Si](C)(C)[O:6][CH2:7][C:8]([CH3:29])([CH3:28])[C:9]#[C:10][C:11]1[CH:12]=[CH:13][C:14]2[N:18]=[C:17]([CH3:19])[N:16]([C:20]3[N:25]=[CH:24][N:23]=[C:22]([NH2:26])[N:21]=3)[C:15]=2[CH:27]=1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[NH2:26][C:22]1[N:23]=[CH:24][N:25]=[C:20]([N:16]2[C:15]3[CH:27]=[C:11]([C:10]#[C:9][C:8]([CH3:28])([CH3:29])[CH2:7][OH:6])[CH:12]=[CH:13][C:14]=3[N:18]=[C:17]2[CH3:19])[N:21]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 681816574-{6-[4-(Tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-but-1-ynyl]2-methyl-benzoimidazol-1-yl}-[1,3,5]triazin-2-ylamine

Product 1

HCID 681816814-[3-(4-amino-[1,3,5]triazin-2-yl)-2-methyl-3H-benzoimidazol-5-yl]-2,2-dimethyl-but-3-yn-1-olYield 29.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a solution of 4-{6-[4-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-but-1-ynyl]2-methyl-benzoimidazol-1-yl}-[1,3,5]triazin-2-ylamine (140 mg, 0.32 mmol) in THF (10 ml) was added tetrabutyl-ammonium fluoride (170 mg, 0.64 mmol). Then the solution stirred overnight at room temperature. The reaction mixture was washed with water and purified by column to afford the title compound 4-[3-(4-amino-[1,3,5]triazin-2-yl)-2-methyl-3H-benzoimidazol-5-yl]-2,2-dimethyl-but-3-yn-1-ol (5-e) (30 mg, 29%): 1H NMR (400 MHz, DMSO) delta 1.23 (s, 6H), 2.89 (s, 3H), 3.39 (d, J=6.0 Hz, 2H), 5.00 (t, J=5.6 Hz, 2H), 7.29 (dd, J=1.6, 8.4 Hz, 1H), 7.55 (d, J=8.4 Hz, 1H), 7.99 (s, 1H), 8.02 (s, 1H), 8.33 (t, J=0.4 Hz, 1H), 8.65 (s, 1H). LCMS m/z=+323.1 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-02bca188d81248d6928e11b693b898df
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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