Water → HCID 21290286, compound

Participants

Reaction Steps

4-Ethyl-7-methylthieno[2,3-c]pyridin-5-ol (2.00 g, 10.3 mmol) was added to a suspension of NaH (60% in oil, prewashed with hexanes, 0.46 g, 11.4 mmol) in DMF (30 ml) and stirred at room temperature for two hours. To this was added a mixture of dimethylaminoethylchloride hydrochloride (3.0 g, 20.6 mmol) and NaH (60% in oil, prewashed with hexanes, 546 mg, 22.8 mmol) in DMF (30 ml). The reaction mixture was stirred for two days at room temperature, poured into H2O (300 ml) and extracted with CH2Cl2 (3×200 ml). The combined organic phases were washed with H2O (2×200 ml) and dried over MgSO4. The solvent was removed in vacuo to give an oil (3 g), which was purified by flash chromatography on silica gel 60 (100 g) eluted with 7% MeOH in CH2Cl2 to give an oil (1.5 g, 56% yield). The product was dissolved in CH2Cl2 (100 ml), washed with 1N aqueous NaOH (2×100 ml) and dried over MgSO4. The solvent was removed in vacuo to give the product (0.950 g, 35% yield) as a yellow oil; IR (neat) 1590 and 1440 cm-1 ; mass spectrum m/z 264 (M+); 1H NMR (CDCl3) δ 1.18 (t, J=7 Hz, 3H, CH2CH3), 2.35 (s, 6H, N(CH3)2), 2.63 (s, 3H, 7-CH3), 2.63-3.10 (m, 4H, CH2CH2N, CH2CH3), 4.53 (t, J=6 Hz, 2H, CH2CH2N), 7.27 and 7.53 each (d, J=5 Hz, 1H, thiophene-H).

Provenance & Evidence