3,5-Dimethylaniline → N-(3,5-dimethylphenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine

Participants

Reaction Conditions

Reaction Steps

2-(Methylsulfonyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidine (1-3, 100 mg, 0.33 mmol) and 3,5-dimethylaniline (0.21 ml, 1.66 mmol) were combined neat and heated to 100° C. After 1 hour the mixture was heated to 130° C. After 1 hour, the reaction was partitioned between a pH 5.2 citrate solution and DCM. The aqueous phase was extracted 2× with DCM and the combined organic extracts were dried over Na2SO4, filtered, concentrated and cooled to room temperature. Purification by reverse phase HPLC (5-100% CH3CN/H2O+0.1% TFA) was followed by purification by flash column chromatography (2% MeOH/CH2Cl2) gave the title compound as a white solid. 1H-NMR (300 MHz, CDCl3) δ 8.27 (d, J=5.5 Hz, 1H), 7.66 (d, J=1.2 Hz, 1H), 7.53 (m, 2H), 7.40 (m, 4H), 7.18 (m, 2H), 7.11 (s, 1H), 6.74 (s, 1H), 6.25 (d, J=5.5 Hz, 1H), 2.32 (s, 6H). mp=183° C.

Provenance & Evidence