Sodium hydride → HCID 25099272, compound

Participants

Reaction Steps

A solution of 2-phenyl-pyrimidine-5-carboxylic acid piperazin-1-ylamide dihydrochloride (0.43 mmol) and NaH (60%, 2.15 mmol) in DMF (10 mL) is stirred under N2 at rt for 20 min. 2-Chloro-1-morpholin-4-yl-ethanone (0.65 mmol)) is added and the reaction mixture is stirred at rt overnight. The reaction mixture is quenched with water, and extracted with EtOAc. The organic layer is separated, dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 0-4% methanol in DCM to afford 2-phenyl-pyrimidine-5-carboxylic acid [4-(2-morpholin-4-yl-2-oxo-ethyl)-piperazin-1-yl]-amide (24 mg, 14%) as a solid. MS: 411 (M+H); 1H NMR (300 MHz, CDCl3): δ 2.85-3.10 (m, 2H), 3.60-4.00 (m, 12H), 4.46 (d, 2H), 4.84 (s, 2H), 7.44-7.62 (m, 3H), 8.34-8.58 (m, 2H), 9.20-9.38 (d, 2H). IC50=831.5 nM.

Provenance & Evidence