Tetrabutylammonium Fluoride → HCID 46841275, compound

HRID 1846330Notes

Reaction equation

HRID 1846330 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:26][CH2:27][CH2:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[N:45]([C:46]3[CH:51]=[CH:50][C:49]([CH:52]([CH2:54][CH3:55])[CH3:53])=[CH:48][CH:47]=3)[C:44](=[O:56])[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[N:37]=2)=[CH:32][C:31]=1[CH3:57])(C(C)(C)C)(C)C>C1COCC1>[CH:52]([C:49]1[CH:48]=[CH:47][C:46]([N:45]2[C:44](=[O:56])[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[N:37]=[C:36]2[C:33]2[CH:34]=[CH:35][C:30]([O:29][CH2:28][CH2:27][OH:26])=[C:31]([CH3:57])[CH:32]=2)=[CH:51][CH:50]=1)([CH2:54][CH3:55])[CH3:53]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86659812HCID 86659812, compound

Product 1

HCID 46841275HCID 46841275, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1 M THF solution of TBAF (1.7 mL, 1.70 mmol) was added to a solution of 2-(4-(2-(tert-butyldimethylsilyloxy)ethoxy)-3-methylphenyl)-3-(4-sec-butylphenyl)quinazolin-4(3H)-one (0.320 g, 0.59 mmol) in THF (2 mL). The mixture was stirred at room temperature for 1 hour and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 10% to 90% EtOAc in heptane, afforded the title compound, as a white solid (0.175 g, 69%). 1H-NMR (300 MHz, DMSO-d6): δ 8.15-8.18 (m, 1H), 7.80-7.95 (m, 1H), 7.74 (d, J=7.7 Hz, 1H), 7.49-7.64 (m, 1H), 7.01-7.25 (m, 6H), 6.72 (d, J=8.5 Hz, 1H), 4.81 (t, J=5.5 Hz, 1H), 3.80-3.97 (m, 2H), 3.56-3.73 (m, 2H), 2.54-2.67 (m, 1H), 1.99 (s, 3H), 1.32-1.66 (m, 2H), 1.17 (d, J=6.9 Hz, 3H), 0.67 (t, J=7.3 Hz, 3H). MS (APCI) m/z: 429 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. customPurification by flash chromatography on silica gel
  3. washeluting with 10% to 90% EtOAc in heptane

Sources & evidence

ORD record
ord-89493148fd3342e3822f400e55842e3d
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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