تفاعل #75477

معادلة التفاعل

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

N-(3-nitro-phenyl)-guanidine nitrate

NaOH

→

title compound

المردود 46.1%

{4-(2,4-Dimethyl-thiazol-5-yl)-pyrimidin-2-yl}-(3-nitro-phenyl)-amine

المردود 46.1%

المذيبات

2-methoxyethanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture was refluxed under N2 for 20 h
2. 2
   أخرىThe solvent was evaporated
3. 3
   أخرىthe residue was purified by flash chromatography (EtOAc/PE, 5:1) and recrystallisation from EtOAc/MeOH

الإجراء التجريبي

A mixture of 3-dimethylamino-1-(2,4-dimethyl-thiazol-5-yl)-propenone (1.0 mmol, 0.21 g) and N-(3-nitro-phenyl)-guanidine nitrate (1.0 mmol, 0.24 g) in 2-methoxyethanol (5 mL) was treated with NaOH (40 mg). The reaction mixture was refluxed under N2 for 20 h. The solvent was evaporated and the residue was purified by flash chromatography (EtOAc/PE, 5:1) and recrystallisation from EtOAc/MeOH to afford the title compound as a yellow solid (151 mg, 46%). M.p. 176-178° C. LC−MS: m/z=328 (M+1). C15H13N5O2S requires: C, 55.03; H, 4.00; N, 21.39; found: C, 54.67; H, 3.88; N, 21.77. 1H-NMR (300 MHz, CDCl3) δ2.72 (s, 3H, CH3), 2.74 (s, 3H, CH3), 7.06 (d, 1H, J=5.3 Hz, pyrimidinyl-H), 7.74-7.92 (m, 3H, Ph-H), 8.46 (d, 1H, J=5.3 Hz, pyrimidinyl-H), 8.91 (t, 1H, J=4.3, 2.1 Hz, Ph-H).

المصدر