Tetrabutylammonium Fluoride → HCID 15840656, compound

HRID 342594Notes

Reaction equation

[F:1][C:2]([F:37])([F:36])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][N:20]2[C:25](=[O:26])[CH:24]=[CH:23][N:22](COCC[Si](C)(C)C)[C:21]2=[O:35])[CH2:13][CH2:12]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[F:36][C:2]([F:1])([F:37])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][CH2:19][N:20]2[C:25](=[O:26])[CH:24]=[CH:23][NH:22][C:21]2=[O:35])[CH2:15][CH2:16]1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of the 3-(3-{4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl}-propyl)-1-[2-(trimethylsilyl)ethoxymethyl]-2,4(1H,3H)-pyrimidinedione (273 mg, 0.5 mmol), prepared as in Example 25, tetrabutylammonium fluoride (2 mmol) and THF (5 mL) was stirred 24 hours at 25° C. The reaction mixture then was concentrated and the residue was purified by column chromatography on silica gel eluting with ethyl acetate to give 3-(3-{4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl}propyl)-2,4(1H,3H)-pyrimidinedione (160 mg, 0.39 mmol). The free base was recrystallized from a solution of hydrogen chloride in ethanol to give 3-(3-{4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl}propyl)-2,4(1H,3H)-pyrimidinedione hydrochloride, m.p. 247°-249° C. Anal.: Calcd. for C19H23F3N4O3.(HCl)2 : C, 47.01; H, 5.19; N, 11.54%; Found: C, 46.84; H, 5.18; N, 11.34%.

Workup

concentrationThe reaction mixture then was concentrated
customthe residue was purified by column chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record: ord-fa492a257f64427ba29c877af14f8c7b
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05859014

Reaction notes

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