Sodium triacetoxyborohydride → HCID 59605579, compound

Participants

Reaction Steps

A mixture of 2-(2-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine-8-carbaldehyde (0.155 g, 0.395 mmol), 4-(3-fluoroazetidin-1-yl)piperidine (0.075 g, 0.474 mmol) and 4 Å molecular sieves (0.5 g) in DCE (6 mL) was stirred for 3 h at room temperature. Sodium triacetoxyborohydride (0.168 g, 0.79 mmol) was added and the reaction mixture was stirred for 72 h at room temperature. The reaction mixture was filtered through Celite and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography (Si—PPC, MeOH:DCM, gradient 0:100 to 15:85) to give 608 as a white solid (0.177 g, 84%). LCMS (Method I): RT=2.25 min, [M+H]+ 534.2 1H NMR (400 MHz, DMSO-d6): δ 8.03-7.98 (m, 1 H), 7.65-7.60 (m, 1 H), 7.27-7.21 (m, 2 H), 5.20-5.00 (m, 1 H), 4.50-3.96 (m, 4 H), 3.80 (s, 3 H), 3.80-3.74 (m, 4 H), 3.75 (s, 2 H), 3.56-3.45 (m, 2 H), 3.26 (q, J=7.4 Hz, 2 H), 3.06-2.94 (m, 2 H), 2.78-2.68 (m, 2 H), 2.19-2.09 (m, 2 H), 2.07 (s, 1 H), 1.66-1.57 (m, 2 H), 1.33 (t, J=7.4 Hz, 3 H), 1.25-1.12 (m, 2 H)

Provenance & Evidence