Dimethylformamide → HCID 178516344, compound

Participants

Reaction Steps

In a round-bottomed flask, 1.3 g of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate are introduced into 10 ml of dimethylformamide and then 10 ml of pyridine, 1.44 g of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride and 1.87 g of 4-bromobenzene-1,2-diamine are added. The reaction mixture is stirred at ambient temperature overnight and is then concentrated to dryness under reduced pressure. The residue is taken up in 40 ml of acetic acid and brought to reflux for 4 hours, then concentrated under reduced pressure. 100 ml of water are then added and a saturated aqueous solution of sodium bicarbonate is added until a pH in the region of 7 is obtained. 200 ml of ethyl acetate are then added and the resulting mixture is stirred for 1 hour. The precipitate formed is filtered then purified by silica gel column chromatography, elution being carried out with a gradient of the eluent CH2Cl2/MeOH: 80/20 in dichloromethane of 0% to 100% in 25 minutes. 560 mg of 2-[(5-bromo-1H-benzimidazol-2-yl)methyl]-6-(morpholin-4-yl)pyrimidin-4(3H)-one are obtained in the form of an off-white solid, the characteristics of which are the following:

Provenance & Evidence