Methyl iodide → HCID 19006278, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring suspension of sodium hydride (0.05 9, 1.25 mmol, 60% dispersion in mineral oil) in 20 mL of DMF was added dropwise a solution of 7-(benzoylamino)-4,9-dihydro-4-methyl-9-oxopyrazolo-[5,1-b]quinazoline-2-carboxylic acid, ethyl ester (0.40 g, 1.02 mmol, Example 2) in 30 mL of DMF. The mixture was stirred for 30 minutes at 0° C. followed by dropwise addition of iodomethane (0.07 mL, 1.12 mmol). The ice-bath was removed, the mixture was stirred at room temperature for 2 hours, then concentrated to a yellow solid. The solid was dissolved into water, acidified to a pH of about 7 with a saturated solution of potassium phosphate, monobasic, and extracted into chloroform (2×50 mL). The combined chloroform extract was dried (MgSO4), filtered, and concentrated. Medium pressure chromatography (silica gel, 2.5% methanol in chloroform) of the crude afforded 0.22 g (52%) of the title compound as its ethyl ester; yellow solid, mp 214°-217° C.

Provenance & Evidence