Reaction #75483

Reaction equation

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

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

NaOH

→

title compound

Yield 17.8%

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

Yield 17.8%

Solvents

2-methoxyethanol

Conditions

Workup

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

Procedure

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).

Source