4-Chloroaniline → 2-[(4-chlorophenyl)amino]-6-(2,6-dichlorophenyl)-8-methyl-7H,8H-pyrido[2,3-d]pyrimidin-7-one

HRID 3194

Reaktionsgleichung

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:22](=[O:23])[N:21]([CH3:24])[C:12]2[N:13]=[C:14](S(C)(=O)=O)[N:15]=[CH:16][C:11]=2[CH:10]=1.[Cl:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1>C(OCC)(=O)C>[Cl:25][C:26]1[CH:32]=[CH:31][C:29]([NH:30][C:14]2[N:15]=[CH:16][C:11]3[CH:10]=[C:9]([C:3]4[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=4[Cl:8])[C:22](=[O:23])[N:21]([CH3:24])[C:12]=3[N:13]=2)=[CH:28][CH:27]=1

Komponenten

Reaktionsbedingungen

Temperatur: 238 °C

Versuchsvorschrift

A mixture of 0.113 g (0.29 mmol) of 6-(2,6-dichlorophenyl)-2-methanesulfonyl-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 39 in 0.50 g (3.90 mmol) of 4-chloroaniline was heated, with stirring, at the boiling point (238° C.) for 5 minutes. Ethyl acetate (3 mL) was added to the cooled dark blue reaction solution. Petroleum ether (3 mL) was added to completed precipitation of a dark solid. This was filtered and washed with 50% hexane-ethyl acetate; wt 0.078 g. The crude solid was purified to remove dark colors by silica gel chromatography, eluting with chloroform and then 50% hexane-ethyl acetate to obtain pure crystalline product; wt 0.056 g; mp 255°-256° C.

Aufarbeitung

temperaturewas heated
customprecipitation of a dark solid
filtrationThis was filtered
washwashed with 50% hexane-ethyl acetate
customThe crude solid was purified
customto remove dark colors by silica gel chromatography
washeluting with chloroform
custom50% hexane-ethyl acetate to obtain pure crystalline product

Quellen und Nachweise

ORD-Eintrag: ord-2fa6392e84c549aa85701a13e6abad4d
Quelldatensatz: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05733914

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