2,4-Dichloropyrimidine → 4-(6-Chloro-benzo[b]thiophene-2-sulfonyl)-1-[1-(2-chloro-pyrimidin-4-yl)-piperidin-4-ylmethyl]-piperazin-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-1-piperidin-4-ylmethyl-piperazin-2-one (40 mg, 0.094 mmole) in n-butanol (1.0 mL) is added 2,4-dichloropyrimidine (14, 0.094 mmole) and diisopropylethylamine (0.016 mL, 0.094 mmole) and this mixture is heated at 110° C. for 4 hours. The reaction is concentrated and purified by column chromatography (silica, 25% ethyl acetate/dichloromethane) to yield 4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-1-[1-(2-chloro-pyrimidin-4-yl)-piperidin-4-ylmethyl]-piperazin-2-one. 1H NMR (300 MHz, CDCl3) d 8.01 (d, 1H), 7.89-7.87 (m, 3H), 7.48 (dd, 1H), 6.35 (d, 1H), 4.41-4.20 (m, 2H), 3.87 (s, 2H), 3.48 (s, 4H), 3.28 (dd, 2H), 2.05-1.95 (m, 1H), 1.67 (d, 2H), 1.31-1.20 (m, 2H); MS (Ion spray) 542 (M+H)+.

Provenance & Evidence