1,3-Benzodioxol-5-amine → 2-(Benzo[1,3]dioxol-5-ylamino)-6-(2,6-dichlorophenyl)-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 3195

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.[CH2:25]1[O:34][C:33]2[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][C:27]=2[O:26]1>C(OCC)(=O)C>[O:34]1[C:33]2[CH:32]=[CH:31][C:29]([NH:30][C:14]3[N:15]=[CH:16][C:11]4[CH:10]=[C:9]([C:3]5[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=5[Cl:8])[C:22](=[O:23])[N:21]([CH3:24])[C:12]=4[N:13]=3)=[CH:28][C:27]=2[O:26][CH2:25]1

Komponenten

Reaktionsbedingungen

Temperatur: 200 °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 and 0.50 g (3.70 mmol) of 3,4-methylenedioxyaniline was heated, with stirring, in a 200° C. oil bath. The resulting solution was heated for 5 minutes and cooled to room temperature. Ethyl acetate (2 mL) was added, and some traces of solids were filtered. The crystals that slowly developed in the filtrate were filtered and washed with 2 mL of ethyl acetate; wt 0.080 g. The 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 0.054 g; mp 240°-241° C.

Aufarbeitung

temperaturewas heated
temperatureThe resulting solution was heated for 5 minutes
temperaturecooled to room temperature
filtrationsome traces of solids were filtered
filtrationwere filtered
washwashed with 2 mL of ethyl acetate
customThe 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-229e6ead42474df5b581ec87f76dc9f1
Quelldatensatz: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05733914

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