Potassium Carbonate → 5-(1,4,5,6-Tetrahydropyrimidin-1-yl)-3-methyl-2-nitro aniline

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2.0 g (11.76 mmol) of 5-fluoro-3-methyl-2-nitro-aniline in 10 mL of DMSO was added 1.2 g (14.11 mmol) of 1,4,5,6-tetrahydropyrimidine, and 2.43 g (17.64 mmol) of potassium carbonate, and the mixture was heated at 100° C. for 10 hrs, cooled, diluted with water, and extracted with Ethylacetate containing 5% methanol. The combined organic extract was washed with water, brine and dried (Na2SO4). Evaporation of the solvent furnished the residue, which was chromatographed (20% of 2M ammonia in methanol and dichloromethane) to produce 1.85 g (67%) of the product as red solid. 1H NMR (400 MHz, CD3OD) δ 7.89 (1H, s), 6.53 (1H, d, J=2.57 Hz), 6.44 ((1H, d, J=2.1 Hz), 7.04 (1H, d, J=2.1 Hz), 3.70 (2H, t, J=6.0 Hz), 3.41 (2H, t, J=5.65 Hz, 2.43 (3H, s), 2.05 (2H, m) LCMS (M+H)+ m/z 235 (t=0.78 min).

Provenance & Evidence