Diisopropylethylamine → HCID 178462584, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(1-ethyl-1H-1,3-benzodiazol-2-yl)ethan-1-amine dihydrochloride (346 mg, 1.32 mmol), 6-chloro-9H-purine (204 mg, 1.32 mmol) and DIPEA (904 μL, 5.28 mmol) in n-butanol (2.5 mL) was stirred in a sealed tube for 3 h at 120° C. After cooling to RT, the crude reaction mixture was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH. The product containing fractions were combined and concentrated under reduced pressure. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM) and triturated with a mixture EtOAc/diethyl ether, filtered and further washed with additional diethyl ether affording racemic 107 as a pale pink solid (182 mg, 45%). LCMS: RT 2.18 min [M+H]+ 308.1. 1H NMR (CDCl3, 400 MHz): δ 8.51 (1H, s), 7.95 (1H, s), 7.76 (1H, d, J=7.17 Hz), 7.39-7.34 (1H, m), 7.31-7.15 (3H, m), 6.03 (1H, br), 4.51-4.39 (1H, m), 4.37-4.26 (1H, m), 1.97-1.80 (4H, m), 1.43 (3H, t, J=7.21 Hz)

Provenance & Evidence