Sodium triacetoxyborohydride → HCID 59606136, compound

Participants

Reaction Steps

A mixture of 2-(2-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine-8-carbaldehyde (165 mg, 0.42 mmol), 1-azetidin-3-ylpyrrolidin-2-one (65 mg, 0.46 mmol) and 4 Å powdered molecular sieves in DCE (4 mL) was stirred at room temperature for 2 h before the addition of sodium triacetoxyborohydride (180 mg, 0.84 mmol). The reaction mixture was stirred for 65 h then filtered through celite, washing with DCM. The organic phase was washed with brine and concentrated in vacuo. The organic phase was dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, MeOH:EtOAc, 0-15%) affording 588 as an orange foam (138 mg, 64%). LCMS (method I): RT 2.42 min [M+H]+ 516.2 1H NMR (CDCl3, 300 MHz): δ 8.00 (m, 1 H), 7.76 (m, 1 H), 7.27 (m, 2 H), 4.83 (t, J=6.9 Hz, 1 H), 4.35 (m, 4 H), 3.89-3.82 (m, 9 H), 3.67-3.54 (m, 4 H), 3.36 (m, 4 H), 2.42 (t, J=8.1 Hz, 2 H), 2.07 (m, 2 H) and 1.45 (t, J=7.5 Hz, 3 H)

Provenance & Evidence