Tetrabutylammonium Fluoride → HCID 11416338, compound

HRID 2105312Notes

Reaction equation

HRID 2105312 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[N:9]([CH2:21][C:22]3[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=3[C:24]#[N:25])[C:10](=[O:20])[C:11]([C:14]#[C:15][Si](C)(C)C)=[CH:12][N:13]=2)[CH2:3]1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[N:9]([CH2:21][C:22]3[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=3[C:24]#[N:25])[C:10](=[O:20])[C:11]([C:14]#[CH:15])=[CH:12][N:13]=2)[CH2:3]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 24760790HCID 24760790, compound

Product 1

HCID 11416338HCID 11416338, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Deprotection of 2-[2-(3-(R)-amino-piperidin-1-yl)-5-trimethylsilylethynyl-6-oxo-6H-pyrimidin-1-ylmethyl]-benzonitrile (168 mg) was carried out by stirring the intermediate in THF (2 mL) with TBAF (1 N in THF, 0.8 mL, 0.8 mmol) for 1 h. The reaction was purified by silica gel chromatography (4 to 8% MeOH/CHCl3) to give 98 mg (71%) of the title compound as a faintly yellow oil/foam. 1H NMR (400 MHz, DMSO-d6): δ 8.01 (s, 1H), 7.81 (dd, 1H, J=7.6, 1.2 Hz), 7.63 (dt, 1H, J=7.6, 1.2 Hz), 7.45 (t, 1H, J=7.6 Hz), 7.19 (d, 1H, J=7.6 Hz), 5.22 (AB q, 2H, J=16.4, 15.2 Hz), 4.13 (s, 1H), 3.25-3.46 (m, 2H), 2.82-2.89 (m, 1H), 2.70-2.77 (m, 1H), 2.58-2.63 (m, 1H), 1.74-1.82 (m, 1H), 1.63-1.71 (m, 1H), 1.45-1.57 (m, 1H), 1.11-1.19 (m, 1H). MS (ES) [m+H] calc'd for C19H19N5O, 334; found 334.

Workup

  1. customThe reaction was purified by silica gel chromatography (4 to 8% MeOH/CHCl3)

Sources & evidence

ORD record
ord-d195ef4069c74383a192260e155bbce9
Source dataset
uspto-grants-2009_08
Patent number
US07579357B2

Reaction notes

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