Diisopropylethylamine → 8-(8-Oxa-bicyclo[3.2.1]oct-6-en-3-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione

Participants

Reaction Steps

To a solution of 8-oxa-bicyclo[3.2.1]oct-6-ene-3-carboxylic acid (0.25 mmol, 0.0386 g), HATU (0.25 mmol, 0.0952 g), and 5,6-diamino-1,3-dipropyl-1H-pyrimidine-2,4-dione hydrochloride (Daly, J. W. et al., J. Med. Chem., 1985, 28 (4), 487) (0.25 mmol, 0.0658 g) in DMF (2.5 ml) was added iPr2NEt (0.75 mmol, 0.13 ml). The reaction was stirred overnight at room temperature. It was concentrated at the pump to remove DMF. The residue was dissolved in EtOAc and washed with 1N HCl, 5% NaHCO3, and brine and dried (MgSO4). Filtration and evaporation followed by flash column chromatography, eluting with a THF/CH2Cl2 gradient provided the desired product (0.067 g, 74%) as an oil that solidified on standing. 1H NMR (300 MHz, CDCl3): 0.90 (t, 3H, J=7.4 Hz), 0.97 (t, 3H, J=7.3 Hz), 1.53-1.72 (m, 6H), 1.95-2.03 (m, 2H), 3.0 (br m, 1H), 3.82-3.91 (m, 4H), 4.79 (br s, 2H), 6.18 (s, 2H).

Provenance & Evidence