Stannous chloride dihydrate → 3-[4-chloro-2-diazanyl-6-fluoro-3-methoxyphenyl]-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione

HRID 1265393

Reaktionsgleichung

[NH2:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([Cl:10])[CH:5]=[C:4]([F:11])[C:3]=1[N:12]1[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]1=[O:24].[N:25]([O-])=O.[Na+].O.O.Cl[Sn]Cl>Cl>[Cl:10][C:6]1[CH:5]=[C:4]([F:11])[C:3]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]2=[O:24])=[C:2]([NH:1][NH2:25])[C:7]=1[O:8][CH3:9]

Komponenten

Reaktionsbedingungen

Temperatur: -15 °C

Versuchsvorschrift

3-(2-Amino-4-chloro-6-fluoro-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione (0.9 g, 2.4 mmol) was dissolved in conc. hydrochloric acid (5 ml) and the mixture cooled to −15° C., a solution of NaNO2 (0.2 g in 2 ml of H2O) was added slowly. After stirred for 20 min, a solution of SnCl2.2H2O (1.5 g in 4 ml of conc. hydrochloric acid) was added and the reaction continued at −15° C. for 30 min, then at room temperature for 30 min. The aqueous mixture was extracted with ethyl acetate (5 ml×3) and the organic phase washed with brine and dried over Na2SO4. Column chromatography was used to purify the product (silica gel, hexane/ethyl acetate=6/4). Yield: 0.5 g, 1.3 mmol.

Aufarbeitung

waitthe reaction continued at −15° C. for 30 min
waitat room temperature for 30 min
extractionThe aqueous mixture was extracted with ethyl acetate (5 ml×3)
washthe organic phase washed with brine
dry with materialdried over Na2SO4
customto purify the product (silica gel, hexane/ethyl acetate=6/4)

Quellen und Nachweise

ORD-Eintrag: ord-cd7ad54740d3405e900f7de4a16e19a7
Quelldatensatz: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06545161B2

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