Sodium triacetoxyborohydride → HCID 59605922, compound

Participants

Reaction Steps

A mixture of 2-(2-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine-8-carbaldehyde (0.0725 g, 0.18 mmol), 3,3-difluoro-[1,3′]biazetidinyl (0.033 g, 0.22 mmol) and 4 Å molecular sieves (0.2 g) in DCE (5 mL). The reaction mixture was stirred for 7 h at room temperature. Sodium triacetoxyborohydride (0.079 g, 0.37 mmol) was added and the reaction mixture was stirred for 18 h at room temperature. The suspension was filtered through Celite and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography (Si—PPC, MeOH:EtOAc, gradient 0:100 to 40:60) to give 562 as a yellow solid (0.075 g, 78%). LCMS (Method I): RT=2.66 min, [M+H]+ 524.2 1H NMR (400 MHz, DMSO-d6): δ 8.03-7.98 (m, 1 H), 7.65-7.60 (m, 1 H), 7.27-7.20 (m, 2 H), 4.50-3.96 (m, 4 H), 3.88 (s, 2 H), 3.86-3.67 (m, 7 H), 3.71-3.55 (m, 4 H), 3.48-3.39 (m, 1 H), 3.37-3.35 (m, 2 H), 3.26 (q, J=7.5 Hz, 2 H), 3.06 (dd, J=7.5, 5.3 Hz, 2 H), 1.33 (t, J=7.5 Hz, 3 H)

Provenance & Evidence