Sodium Hydroxide → HCID 17986365, compound

Participants

Reaction Steps

A solution of 600 mg (1.35 mmol) of a mixture of 4-nitro-thiophene-2-sulfonic acid [2-(5-bromo-2-chloro-pyrimidin-4-ylamino)-ethyl]-amide and 5-nitro-thiophene-2-sulfonic acid-[2-(5-bromo-2-chloro-pyrimidin-4-ylamino)-ethyl]-amide (ratio 10/6) in 40 ml of THF is mixed under argon at room temperature with 6.4 ml of a 15% solution of Ti(III)Cl in approximately 10% hydrochloric acid. After 46 hours, the reaction solution is mixed again with 2.0 ml of Ti(III)Cl solution and stirred for another 7 hours. The batch is made basic with 2N NaOH solution and then filtered. The filter cake is rewashed 2× with 50 ml of ethyl acetate/MeOH (30 ml/20 ml) in each case. The filtrate is concentrated by evaporation in a rotary evaporator and then extracted with ethyl acetate (2×). The combined organic phases are filtered through a Whatman filter and concentrated by evaporation. The residue is purified by chromatography (hexane/ethyl acetate 1:4). 178 mg (0.43 mmol, corresponding to 32% of theory) of the product is obtained.

Provenance & Evidence