Methanol → HCID 78031603, compound

Participants

Reaction Steps

Cu(OAc)2 (6.02 g, 33.13 mmol, 1.1 eq.) was added to a mixture of [3-(tert-butoxycarbonyl-{1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethyl}-amino)-propyl]-carbamic acid tert-butyl ester (15.18 g, 30.12 mmol, 1 eq.), 4-amino-5-iodo-1H-pyrimidin-2-one (7.85 g, 33.13 mmol, 1.1 eq.), MeOH (400 mL) and H2O (100 mL), followed by N,N,N′,N′-tetramethyl-ethane-1,2-diamine (7.69 g, 66.26 mmol, 2.2 eq.). The Mixture was stirred at RT under air for 48 h (weekend) before concentrated to a volume ca. 130 mL. The residue was diluted with CH2Cl2 (200 mL). The CH2Cl2 extract was washed with brine and concentrated. The crude product was purified by flash chromatography (CH2Cl2:MeOH:NH4OH/35:1:0.01) to afford [3-({1-[4-(4-amino-5-iodo-2-oxo-2H-pyrimidin-1-yl)-phenyl]-ethyl}-tert-butoxycarbonyl-amino)-propyl]-carbamic acid tert-butyl ester (16.06 g, 87%).

Provenance & Evidence