Reaction #75479

Reaction equation

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

N-(4-fluoro-phenyl)-guanidine nitrate

NaOH

→

title compound

Yield 89.6%

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

Yield 89.6%

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/PE, 2:1) and recrystallisation from EtOAc/PE

Procedure

To a mixture of 3-dimethylamino-1-(2,4-dimethyl-thiazol-5-yl)-propenone (1.0 mmol, 0.21 g) and N-(4-fluoro-phenyl)-guanidine nitrate (2.0 mmol, 0.44 g) in 2-methoxyethanol (5 mL) was added 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/PE, 2:1) and recrystallisation from EtOAc/PE to afford the title compound as brown crystals (269 mg, 89%). 1H-NMR (300 MHz, CDCl3) δ2.69 (s, 3H, CH3), 2.71 (s, 3H, CH3), 6.93 (d, 1H, J=5.3 Hz, pyrimidinyl-H), 7.03 (m, 2H, Ph-H), 7.58 (m, 2H, Ph-H), 8.40 (d, I H, J=5.3 Hz, pyrimidinyl-H).

Source