Water → HCID 21891803, Verbindung

HRID 858081

Reaktionsgleichung

Cl.[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][NH2:13])=[CH:7][CH:6]=1)([O-:4])=[O:3].[CH2:14]([N:18]1[C:23](Cl)=[CH:22][C:21](=[O:25])[N:20]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[F:33])[C:19]1=[O:34])[CH2:15][CH2:16][CH3:17].C(N(CC)CC)C.O>CN1CCCC1=O>[CH2:14]([N:18]1[C:23]([NH:13][CH2:12][CH2:11][C:8]2[CH:7]=[CH:6][C:5]([N+:2]([O-:4])=[O:3])=[CH:10][CH:9]=2)=[CH:22][C:21](=[O:25])[N:20]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[F:33])[C:19]1=[O:34])[CH2:15][CH2:16][CH3:17]

Komponenten

Reaktionsbedingungen

Temperatur: 75 °C

Versuchsvorschrift

A mixture of 2-(4-nitro-phenyl)-ethylamine hydrochloride salt (Fluka) (7.85 g, 38.7 mmol), 1-butyl-6-chloro-3-(2-fluorobenzyl)-1H-pyrimidine-2,4-dione (8.0 g, 25.8 mmol) and triethylamine (10.7 mL, 77 mmol) in N-methyl-pyrrolidin-2-one (200 mL) was stirred at 75° C. for 16 hours. The reaction was then mixed with water and extracted with ethyl acetate (3×). The combined ethyl acetate layers were dried (magnesium sulfate) and concentrated. Column chromatography afforded 1-butyl-3-(2-fluorobenzyl)-6-[2-(4-nitro-phenyl)-ethylamino]-1H-pyrimidine-2,4-dione (4.7 g, 41%) as a solid. 1H NMR (CDCl3, 200 MHz) δH 0.84 (t, 3H), 1.11–1.50 (m, 4H), 3.10 (t, 2H), 3.48 (m, 2H), 3.70 (t, 2H), 4.36 (t, 1H), 4.94 (t, 1H), 5.20 (s, 2H), 6.95–7.10 (m, 2H), 7.17–7.30 (m, 2H), 7.39 (d, 2H), 8.20 (d, 2H).

Aufarbeitung

extractionextracted with ethyl acetate (3×)
dry with materialThe combined ethyl acetate layers were dried (magnesium sulfate)
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-079bf66084924f779f454b534324519e
Quelldatensatz: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07148229B2

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