Adenine → 3-(6-Amino-9h-purin-9-yl)propanenitrile

Participants

Reaction Conditions

Reaction Steps

To a suspension of 57% NaH in mineral oil (0.962 g, 22.8 mmol) in dry DMF (100 mL) was added 10 (3.40 g, 24.9 mmol) under nitrogen and the mixture was heated at 80° C. for 1.0 h. A solution of 3-bromopropionitrile (2.81 g, 21.0 mmol) in DMF (5.0 mL) was added at 25° C. and the reaction was heated at 65° C. for 17 h. It was then diluted with EtOAc (250 mL) and 5% aqueous HCl solution (150 mL). The organic layer was separated and then washed with water (4×100 mL). It was dried over MgSO4 (s) and concentrated under reduced pressure. Purification of the residue was carried out by use of column chromatography (EtOAc/hexanes=7.5:2.5) to afford compound 15 (3.510 g, 18.67 mmol) in 75% yield: mp 148-150° C.; Rf(hexanes/EtOAc=1:2) 0.38; UV (EtOH) λmax 260 (ε 13,900); 1H NMR (CD3OD) δ 2.92 (t J=5.8 Hz, 2 H, CH2CN),3.43 (t, J=5.8 Hz, 2 H, CH2N), 8.35 (s, 1 H, HC2), 8.69 (s, 1 H, HC8); MS m/z 188 (M+).

Provenance & Evidence