Water → HCID 21290302, compound

Participants

Reaction Steps

3-(N,N-Dimethylamino)propylchloride hydrochloride (5.51 g, 34.9 mmol) and sodium hydride (60% in oil, 1.55 g, 38.8 mmol, prewashed with pentane) in DMF (30 ml) were stirred at room temperature for one hour. This solution was then added to a mixture of 4-ethyl-7-methylthieno[2,3-c]pyridin-5-ol (2.9 g, 15.0 mmol) and sodium hydride (60% in oil, 0.60 g, 15.0 mmol, prewashed in pentane) in DMF (30 ml) which had been allowed to react for two hours. The combination was stirred at room temperature for three days, poured into H2O (500 ml), extracted with CH2Cl2 (3×200 ml) and dried over MgSO4. The solvent was removed in vacuo and the product was purified by flash chromatography on silica gel 60 (120 g) using 8% MeOH in CH2Cl2 as the eluant to give the product (2.3 g, 55% yield) as a yellow oil; IR (neat) 1440, 1580 and 2980 cm-1 ; mass spectrum m/z 279 (MH+); 1H NMR (CDCl3) δ 1.20 (t, J=7 Hz, 3H, CH2CH3), 1.68 to 2.90 (m, 6H, CH2CH2N, CH2CH3), 2.27 (s, 6H, N(CH3)2), 2.63 (s, 3H, 7-CH3), 4.43 (t, J=6 Hz, 1H, OCH2CH2), 7.27 and 7.53 each (d, J=6 Hz, 1H, thiophene-H).

Provenance & Evidence