2,4-Hexadienal → 4-ethoxy-7-(4-[{2E,4E}-1-hydroxyhexa-2,4-dienyl]phenyl)-9-methyl-2-piperazin-1-yl-thieno[2,3-d:4,5-d']dipyrimidine

Participants

Reaction Conditions

Reaction Steps

200 mg (0.4 mmol) 7-(4-bromophenyl)-4-ethoxy-9-methyl-2-piperazin-1-yl-thieno[2,3-d:4,5-d′]dipyrimidine was mixed at −80° C. in 50 ml THF with 0.48 ml (1.2 mmol) 2.5 M BuLi solution. After 15 min at this temperature, 112 mg (1.2 mmol) (2E,4E) hexadienal was added. Subsequently, the reaction mixture was heated to −10° C. and the reaction was terminated by addition of 10 ml saturated NaHCO3. The organic solvent was removed and the aqueous phase was extracted with CH2Cl2. Following flash chromatographic purification (CH2Cl2/methanol, 8:2) 130 mg (63%) of the title compound was obtained. ESI-MS [m/z]: 503, melting point: 149-150° C.

Provenance & Evidence