Reaction #75481

Reaction equation

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

N-(2,4-difluoro-phenyl)-guanidine nitrate

NaOH

→

title compound

Yield 79.0%

(2,4-Difluoro-phenyl)-{4-(2,4-dimethyl-thiazol-5-yl)-pyrimidin-2-yl}-amine

Yield 79.0%

Solvents

2-methoxyethanol

Conditions

Workup

1. 1
   TemperatureAfter 24 h refluxing under N2 the solvent
2. 2
   Otherwas evaporated to dryness
3. 3
   Otherthe residue was purified by flash chromatography (EtOAc/PE, 2:1) and recrystallisation from EtOAc/PE

Procedure

A mixture of 3-dimethylamino-1-(2,4-dimethyl-thiazol-5-yl)-propenone (1.0 mmol, 0.21 g) and N-(2,4-difluoro-phenyl)-guanidine nitrate (2 mmol, 0.47 g) in 2-methoxyethanol (5 mL) was treated with NaOH (40 mg). After 24 h refluxing under N2 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 a brown powder (250 mg, 79%). 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), 7.01 (m, 2H, Ph-H), 7.58 (m, 2H, Ph-H), 8.40 (d, 1H, J=5.3 Hz, pyrimidinyl-H).

Source