تفاعل #75483

معادلة التفاعل

3-Dimethylamino-1-(2,4-dimethyl-thiazol-5-yl)-propenone

N-(4-hydroxy-2-nitro-phenyl)-guanidine nitrate

NaOH

→

title compound

المردود 17.8%

4-{4-(2,4-Dimethyl-thiazol-5-yl)-pyrimidin-2-ylamino}-2-nitro-phenol

المردود 17.8%

المذيبات

2-methoxyethanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture was refluxed under N2 for 24 h
2. 2
   أخرىThe solvent was evaporated to dryness
3. 3
   أخرىthe residue was purified by flash chromatography (EtOAc) and recrystallisation from EtOAc/PE

الإجراء التجريبي

3-Dimethylamino-1-(2,4-dimethyl-thiazol-5-yl)-propenone (1 mmol, 0.21 g) in 2-methoxyethanol (5 mL ) was treated with N-(4-hydroxy-2-nitro-phenyl)-guanidine nitrate (2 mmol, 0.52 g) in the presence of NaOH (40 mg). The reaction mixture was refluxed under N2 for 24 h. The solvent was evaporated to dryness and the residue was purified by flash chromatography (EtOAc) and recrystallisation from EtOAc/PE to afford the title compound as a yellow powder (61 mg). 1H-NMR (300 MHz, CDCl3) δ2.71 (s, 3H, CH3), 2.73 (s, 3H, CH3), 7.01 (d, 1H, J=5.2 Hz, pyrimidinyl-H), 7.18 (m, 1H, Ph-H), 7.64 (m, 1H, Ph-H), 8.42 (d, 1H, J=5.2 Hz, pyrimidinyl-H), 8.75 (d, 1H, J=2.7 Hz, Ph-H), 10.45 (br. s, 1H, OH).

المصدر