4-Methylmorpholine → 4-[4-Methoxy-5-(2-methoxy-phenoxy)-6-(5-methyl-pyridine-2-sulfonylamino)-pyrimidin-2-yl]-pyridine-2-carboxylic acid methyl amide

Participants

Reaction Conditions

Reaction Steps

70 mg of 4-[4-methoxy-5-(2-methoxy-phenoxy)-6-(5-methyl-pyridine-2-sulfonylamino)-pyrimidin-2-yl]-pyridine-2-carboxylic acid, product of example 21, dissolved in DMF (5 ml) was treated at RT with 30 mg of 4-methylmorpholine, then cooled to 0° C. and further treated with 26 mg of 2-chloro-4,6-dimethoxy-1,3,5-triazine followed. The solution was stirred at RT for 90 minutes, then treated with 10 mg of metylamine hydrochloride and stirred for 12 h at RT. The mixture was partitioned between cold diluted HCl and EtOAc. The layers were separated, the organic layer washed with water, dried over Na2SO4 and the solvent was removed in vacuo. The solid residue was triturated with ether, filtered off and dried in a high vacuum to give 4-[4-methoxy-5-(2-methoxy-phenoxy)-6-(5-methyl-pyridine-2-sulfonylamino)-pyrimidin-2-yl]-pyridine-2-carboxylic acid methyl amide as a white crystalline solid. ISN mass spectrum, m/e 535.2 (M−1 calculated for C25H24N6O6S: 535).

Provenance & Evidence