1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 69063750, compound

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Reaction Steps

(2-Chloro-9-isopropyl-9H-purin-6-yl)-(3-nitro-phenyl)-amine (333 mg, 1 mmol), D-valinol (310 mg, 3.0 mmol), and DBU (457 mg, 3.0 mmol) were stirred in NMP (5 mL) overnight at 150° C. under N2. After cooling, the mixture was diluted with H2O (40 mL) and was extracted with CH2Cl2 (3×25 mL). The combined extracts were washed with brine, treated with decolourising charcoal and MgSO4, filtered, and evaporated. The residue was redissolved in DMSO/H2O and chromatographed (Vydac 218TP1022; 9 mL/min, 27.5-37.5% MeCN in 0.1% aq CF3COOH over 40 min). Appropriate peak fractions were pooled and lyophilized to afford the title compound as an orange solid (12.3 mg). Anal. RP-HPLC (Vydac 218TP54; 1 mL/min): tR=15.8 min (27.5-37.5% MeCN in 0.1% aq CF3COOH over 20 min); purity>95% (λ=214 nm). DE-MALDI-TOF MS: [M+H]+=398.5 (C19H25N7O3=399.5).

Provenance & Evidence