Sodium hydride → 4-[4-(4-Fluorophenyl)-2-methyl-5-(2-methylsulfanyl-pyrimidin-4-yl)-3-oxo-2,3-dihydro-pyrazol-1-yl]-piperidine-1 carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-{N′-[2-(4-fluoro-phenyl)-acetyl]-N′-methyl-N-(2-methylsulfanyl-pyrimidine-4-carbonyl)-hydrazino}-piperidine-1-carboxylic acid tert-butyl ester, 10, (1.058 g, 2.05 mmol) in DMF (2 mL) at 0° C. is slowly added NaH (123 mg of a 60% dispersion in mineral oil, 3.07 mmol). The reaction mixture is stirred for 1 hour at 0° C. and then quenched with 0.1 N HCl. The aqueous layer is extracted three times with CH2Cl2 and the combined organic layers are dried (MgSO4), filtered and concentrated in vacuo. Purification over silica (20% MeOH/CHCl3) affords 0.743 g (73% yield) of the diesired product. ESI/MS: 500.2 (M+H).

Provenance & Evidence