Tetrabutylammonium Fluoride → HCID 46841407, compound

HRID 1846333Notes

Reaction equation

HRID 1846333 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]([Cl:52])=[CH:48][CH:47]=3)[C:44](=[O:53])[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[N:37]=2)=[CH:32][C:31]=1[CH3:54])(C(C)(C)C)(C)C>C1COCC1>[Cl:52][C:49]1[CH:50]=[CH:51][C:46]([N:45]2[C:44](=[O:53])[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]([CH3:54])[CH:32]=2)=[CH:47][CH:48]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 674598262-(4-(2-(tert-Butyldimethylsilyloxy)ethoxy)-3-methylphenyl)-3-(4-chlorophenyl)quinazolin-4(3H)-one

Product 1

HCID 46841407HCID 46841407, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1M THF solution of TBAF (1.90 mL, 1.90 mmol) was added to a solution of 2-(4-(2-(tert-butyldimethylsilyloxy)ethoxy)-3-methylphenyl)-3-(4-chlorophenyl)quinazolin-4(3H)-one (0.340 g, 0.65 mmol) in THF (5 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 100% EtOAc in heptane, afforded the title compound as a white solid (0.190 g, 72%). 1H-NMR (300 MHz, DMSO-d6): δ 8.17 (dd, J=6.8, 1.0 Hz, 1H), 7.89 (d, J=6.8 Hz, 1H), 7.75 (d, J=8.8 Hz, 1H), 7.55-7.59 (m, 1H), 7.28-7.48 (m, 4H), 7.21 (d, J=1.5 Hz, 1H), 7.04-7.16 (m, 1H), 6.77 (d, J=8.7 Hz, 1H), 4.81 (t, J=5.7 Hz, 1H), 3.86-4.01 (m, 2H), 3.60-3.77 (m, 2H), 2.06 (s, 3H). MS (APCI) m/z: 407 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. customPurification by flash chromatography on silica gel
  3. washeluting with 10% to 100% EtOAc in heptane

Sources & evidence

ORD record
ord-130f803503224caa8d8250eeb8daed5b
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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