2-Bromo-4-methylaniline → 4-(4-Hydroxyanilino)-6-(2-bromo-4-methylanilino)pyrimidine

HRID 987547

Reaktionsgleichung

Reaktionsgleichung von HRID 987547
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([NH:6][C:7]2[CH:12]=[C:11](Cl)[N:10]=[CH:9][N:8]=2)=[CH:4][CH:3]=1.[Br:16][C:17]1[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:18]=1[NH2:19]>>[OH:1][C:2]1[CH:15]=[CH:14][C:5]([NH:6][C:7]2[CH:12]=[C:11]([NH:19][C:18]3[CH:20]=[CH:21][C:22]([CH3:24])=[CH:23][C:17]=3[Br:16])[N:10]=[CH:9][N:8]=2)=[CH:4][CH:3]=1

Komponenten

3

Edukt 2

HCID 114222-Bromo-4-methylanilineHCID 180091284-(4-Hydroxyanilino)-6-chloropyrimidine

Produkt 1

HCID 180091414-(4-Hydroxyanilino)-6-(2-bromo-4-methylanilino)pyrimidineAusbeute 4 %

Reaktionsbedingungen

Temperatur
195 °C

Versuchsvorschrift

To a solution of 4-(4-hydroxyanilino)-6-chloropyrimidine (Reference Example 5, 5 g) was added 2-bromo-4-methylaniline (7.5 ml) and the reaction mixture was heated at 195° C. for 24 hours. The residue was absorbed onto silica and purified by column chromatography eluting with DCM:MeOH (19:1) to give the title compound (336 mg, 4%). NMR: 2.28 (3H, s), 5.72 (1H, s), 6.68 (2H, d), 7.17 (3H, m), 7.39 (1H, d), 7.48 (1H, s), 8.05 (1H, s), 8.38 (1H, s), 8.65 (1H, s), 9.08 (1H, s); m/z 371 (MH+).

Aufarbeitung

  1. customThe residue was absorbed onto silica
  2. custompurified by column chromatography
  3. washeluting with DCM:MeOH (19:1)

Quellen und Nachweise

ORD-Eintrag
ord-2cd86b8785844026bd2ff6d6d8213924
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06632820B1

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