N,N-Diphenylhydrazine → 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid N',N'-diphenyl-hydrazide

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (500 mg, 2.2 mmol) and N,N-diphenyl-hydrazine (422 mg, 2.2 mmol) in DMF (3 mL) is stirred at 50° C. for 15 min. The mixture is treated with DMTMM (633 mg, 2.2 mmol) and stirred at 50° C. for 3 h. The mixture is diluted with EtOAc (50 mL), and washed with saturated aqueous Na2CO3 (50 mL). The organic layer is separated, dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 75% EtOAc in heptane to afford 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid N′,N′-diphenyl-hydrazide (60 mg, 7%). MS: 399 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 9.04 (s, 1H), 8.30 (d, 1H), 8.15 (m, 1H), 7.61 (m, 1H), 7.44 (m, 1H), 7.35 (m, 4H), 7.22 (m, 4H), 7.04 (m, 2H), 2.64 (s, 3H). IC50=16 nM.

Provenance & Evidence