5-Bromopyrimidine → HCID 23119574, compound

Participants

Reaction Steps

By a procedure analogous to that described in Example 51b, 5,11-dihydro-11-ethyl-8-ethynyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.1 g, 0.36 mmol) was coupled with 5-bromopyrimidine (59 mg, 0.37 mmol) to give 65 mg of 5,11-Dihydro-11-ethyl-5-methyl-8-(5-pyrimidyl)ethynyl-(-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (65 mg). A mixture containing this coupled product (65 mg), cyclohexene (0.07 mL), and 10% palladium on carbon (60 mg) in 2 mL of ethanol was heated in a sealed tube at 95° C. for 5 hours. The reaction mixture was filtered through Celite and concentrated. Purification of the residue by flash chromatography, eluting with methanol/dichloromethane, and recrystallization from ethyl acetate/hexanes provided 27 mg of the title compound, m.p. 142°-143° C.

Provenance & Evidence