Sodium Hydroxide → 4-[4-(2,4-Dimethyl-thiazol-5-yl)-pyrimidin-2-ylamino]-2-nitro-phenol

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) δ 2.71 (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).

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

ORD record

ord-b1ee8aecea3f4e22b77b54c6812a4798

Source dataset

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06531479B2