Bromine → 5-Bromo-4-(1-isopropyl-2-methylimidazol-5-yl)-2-(4-mesylanilino)pyrimidine

HRID 2375276Notizen

Reaktionsgleichung

[Br:1]Br.[CH:3]([N:6]1[C:10]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=3)[N:12]=2)=[CH:9][N:8]=[C:7]1[CH3:28])([CH3:5])[CH3:4]>C(O)(=O)C>[Br:1][C:16]1[C:11]([C:10]2[N:6]([CH:3]([CH3:5])[CH3:4])[C:7]([CH3:28])=[N:8][CH:9]=2)=[N:12][C:13]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)=[N:14][CH:15]=1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

Bromine (50 μl, 0.94 mmol) was added to a solution of 4-(1-isopropyl-2-methylimidazol-5-yl)-2-(4-mesylanilino)pyrimidine (Example 69; 350 mg, 0.94 mmol) in glacial acetic acid (3.5 ml). The mixture was heated at 60° C. for 140 minutes and the volatiles were then removed by evaporation. The residue was azeotroped with water to give a gum, which was then triturated with EtOAc to give a solid (470 mg). This crude product was purified by chromatography on silica gel eluting with DCM/MeOH (98:2 increasing in polarity to 95:5). The purified product was triturated with EtOAc to give the title compound (125 mg, 30%) as a solid. NMR: 1.39 (d, 6H), 2.48 (s, 3H), 3.12 (s, 3H), 4.68 (sept, 1H), 7.20 (s, 1H), 7.81 (d, 2H), 7.92 (d, 2H), 8.79 (s, 1H), 10.28 (br s, 1H); m/z 450.

Aufarbeitung

customthe volatiles were then removed by evaporation
customThe residue was azeotroped with water
customto give a gum, which
customwas then triturated with EtOAc

Quellen und Nachweise

ORD-Eintrag: ord-b34a99b9c66b4cf99efabf672e5e8764
Quelldatensatz: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07465728B2

Notizen zur Reaktion

Wird geladen…