N,N-Dimethylethylenediamine → HCID 178457400, compound

Participants

Reaction Steps

A solution of 5-benzyl-3-bromo-6-(1-bromopropyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (1-3, 5.0 g, 11.7 mmol, 1 equiv) and N,N-dimethylethylenediamine (2.6 g, 29.3 mmol, 2.5 equiv) in ethanol (25 mL) was heated at reflux for 18 h. The reaction was concentrated, and the residue was purified by flash chromatography. Elution with CH2Cl2 to 25% NH3-EtOH/(CH2Cl2 gave 5-benzyl-3-bromo-6-(1-{[2-(dimethylamino)ethyl]amino}propyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (1-4) as a light green foam. 1H NMR (500 MHz, CDCl3) δ 11.1 (bs, 1H), 7.33 (m, 2H), 7.29 (m, 1H), 7.15 (d, J=7 Hz), 5.97 (d, J=16 Hz), 4.71 (d, J=16 Hz), 3.58 (m, 1H), 2.52 (m, 1H), 2.30 (m, 2H), 2.24 (s, 6H), 1.94 (m, 1H), 1.52 (m, 1H), 1.31 (m, 1H), 0.84 (t, J=7 Hz, 3H).

Provenance & Evidence