Diisopropylethylamine → HCID 178461928, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-1-(1-cyclobutyl-6-fluoro-1H-benzoimidazol-2-yl)ethylamine (251 mg, 1.1 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (260 mg, 1.1 mmol) and DIPEA (1.0 mL, 5.5 mmol) in n-butanol (4 mL) was heated at 100° C. for 18 h. After cooling to RT, the volatiles were removed under reduced pressure and the resulting residue was loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH followed by 2M NH3/MeOH. The basic fractions were combined, concentrated in vacuo and the resulting residue purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM) to afford 373 as a white solid (140 mg, 36%). LCMS (Method K): RT 2.93 min [M+H]+ 352.1 1H NMR (DMSO-d6, 400 MHz): δ 12.97 (1H, br), 8.33-7.76 (3H, m), 7.69-7.53 (2H, m), 7.09-6.98 (1H, m), 5.87 (1H, br s), 5.27-5.14 (1H, m), 2.93-2.72 (2H, m), 2.44 (1H, br s), 2.23 (1H, br s), 2.02-1.89 (1H, m), 1.82-1.61 (4H, m)

Provenance & Evidence