Pyridine → Sufugolix

Participants

Reaction Steps

6-(4-aminophenyl)-5-(N-benzyl-N-methylaminomethyl)-1-(2,6-difluorobenzyl)-3-phenylthieno[2,3-d]pyrimidine-2,4(1H, 3H)-dione (0.50 g, 0.84 mmol) was dissolved in dimethyl acetamide (2 ml), pyridine (82 μl, 1.01 mmol) was added thereto, and the mixture was stirred. Phenyl chloroformate (phenyl chlorocarbonate)(126 μl, 1.01 mmol) was added thereto dropwise under ice-cooling, and the mixture was stirred at room temperature for 2 hours. O-methylhydroxylamine hydrochloride (77.2 mg, 92.4 μmol) and triethylamine (336 μl, 2.77 mmol) were added thereto, and the mixture was stirred at 50° C. for 12 hours. Water (30 ml) was added thereto, and the mixture was vigorously stirred. The crystals were filtered, and dried under vacuum at 40° C. to give white crystals of 5-(N-benzyl-N-methylaminomethyl)-1-(2,6-difluorobenzyl)-6-[4-(3-methoxyureido)phenyl]-3-phenylthieno[2,3-d]pyrimidine-2,4(1H, 3H)-dione (0.55 g, 98.2%).

Provenance & Evidence