Sodium hydride → HCID 69486753, compound

Participants

Reaction Conditions

Reaction Steps

The title compound was prepared from 3-(2-dimethylamino-6-methyl-pyrimidin-4-yl)-benzoic acid methyl ester [prepared by the following procedure: A mixture of NaH (50% dispersion in mineral oil, 1.56 g, 32.5 mmol) in 2-propanol (45 ml) was stirred at 50° C. for 10 min. N-methylguanidine hydrochloride (3.3 g, 30 mmol) was added and stirring was continued for 10 min. After the addition of 3-(3-oxo-butyryl)-benzoic acid (3.1 g, 15 mmol), the mixture was stirred at 80° C. for 48 h. After cooling to RT, H2O (100 ml) was added and the mixture was concentrated in vacuum to a volume of ca. 80 ml. The pH was set to 2.5 with 25% HCl and the precipitate was collected, dried and then esterified by stirring in 1N HCl-MeOH (30 ml) for 60 h at RT The crude product was purified by chromatography (silica gel, AcOEt) to give the methyl ester as light yellow solid (0.27 g).] (0.26 g, 1 mmol) by treatment with lithium tert-butyl acetate according to general procedure K (method b). Obtained as a light yellow oil (0.38 g, crude product).

Provenance & Evidence