Reaktion #634723

Reaktionsgleichung

3-Amino-N-(4-nitrophenyl)benzamide

4-chloro-6-methyl-2-pyrimidinylamine

2-amino-6-chloro-4-methylpyrimidine

HCl

→

B2

Ausbeute 98.2%

3-[(2-Amino-6-methyl-4-pyrimidinyl)amino]-N-(4-nitrophenyl)-benzamide hydrochloride

Ausbeute 98.2%

Lösungsmittel

2-ethoxyethanol

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturrefluxed for 1 h. by this time TLC and mass spec
2. 2
   Sonstigecompletion of the reaction
3. 3
   FiltrationThe resulting precipitate was filtered
4. 4
   Waschenwashed with more EtOAc
5. 5
   Sonstigerecrystallized from MeOH/EtOAc/Charcoal/Celite

Vorschrift

3-Amino-N-(4-nitrophenyl)benzamide (B1) (1.0 g, 3.89 mmol) and 4-chloro-6-methyl-2-pyrimidinylamine (A8) (569 mg, 3.89 mmol) were dissolved in warm 2-ethoxyethanol. (20 mL). Two drops c.HCl was then added to the reaction mixture and refluxed for 1 h. by this time TLC and mass spec. showed completion of the reaction. The reaction mixture was diluted with ethyl acetate and cooled to 20° C. The resulting precipitate was filtered, washed with more EtOAc and recrystallized from MeOH/EtOAc/Charcoal/Celite to give B2 (1.531 g, 98%); m.p (MeOH/EtOAc)>300° C.; 1H NMR [(CD3)2SO] δ12.86 (br s, 1 H, N+H), 10.90 (s, 1 H, NH), 10.80 (br s, 1 H, NH), 8.30-8.26 (m, 2H, ArH), 8.11-8.08 (m, 4 H, ArH), 7.80-7.78 (br m, 3 H, ArH & NH2), 7.56 (t, J=7.8 Hz, 1 H, ArH), 2.30 (s, 3 H, CH3); mass APCI+ 365.

Quelle