Molecules 2014, 19
285
23.08 (CH2), 28.72 (CH2), 35.11 (CH2), 53.21 (CH2), 54.96 (CH2), 55.39 (OCH3), 55.48 (OCH3),
120.52 (C-5), 111.83, 112.89, 120.57, 131.06, 147.29, 148.50 (Carom.), 159.97 (C-6), 161.20 (C-4),
164.01 (C-2). ESI-MS, m/z (Rel. Int.): 404 (M + H+, 90).
6-(3,4-Dimethoxybenzyl)-5-ethyl-2-[2-(piperidin-1-yl)ethyl]thiopyrimidin-4(3H)-one (6b) White solid.
1
M.p.: 127–129 °C, Yield: 0.301 g (72%). H-NMR (CDCl3): δ = 0.88 (t, 3H, J = 7.5 Hz, CH3),
1.45–1.47 (m, 2H, CH2), 1.78–1.80 (m, 4H, 2 × CH2), 2.39 (q, 2H, J = 7.5 Hz, CH2),
2.50–2.52 (m, 4H, 2 × CH2), 2.73 (t, 2H, J = 5.0 Hz, CH2), 2.99 (t, 2H, J = 5.0 Hz, CH2), 3.75 (s, 2H, CH2),
3.77 (s, 3H, OCH3), 3.79 (s, 3H, OCH3), 6.70 (s, 2H, Harom.), 6.79 (s, 1H, Harom.), 11.73 (s, 1H, NH).
13C-NMR (CDCl3): δ = 13.23 (CH3), 18.91 (CH2), 24.01, 24.43, 55.44 (Cpiperidin.), 36.21 (CH2), 39.80
(CH2), 55.90 (2 × OCH3), 61.57 (CH2), 122.64 (C-5), 111.09, 112.23, 120.71, 130.88, 147.33, 148.52
(Carom.), 157.07 (C-6), 162.85 (C-4), 164.51 (C-2). ESI-MS, m/z (Rel. Int.): 418 (M + H+, 85).
6-(4-Chlorobenzyl)-5-methyl-2-[2-(morpholin-4-yl)ethyl]thiopyrimidin-4(3H)-one (6c) White solid.
M.p.:158–159 °C, Yield: 0.280 g (74%).1H-NMR (DMSO-d6): δ = 1.95 (s, 3H, CH3), 2.33 (t, 4H,
J = 4.5 Hz, 2 × CH2), 2.46 (t, 2H, J = 7.0 Hz, CH2), 3.13 (t, 2H, J = 7.0 Hz, CH2), 3.54 (t, 4H,
J = 4.5 Hz, 2 × CH2), 3.84 (s, 2H, CH2), 7.24, 7.32 (2 × d, 4H, J = 8.5 Hz, Harom.), 12.61 (s, 1H, NH).
13C-NMR (DMSO-d6): δ = 10.31 (CH3), 26.70 (CH2), 34.17 (CH2), 52.86, 65.97 (Cmorpholin.), 57.35
(CH2); 115.19 (C-5), 128.13, 130.00, 130.58, 137.24 (Carom.), 157.15 (C-6), 159.80 (C-4), 163.34
(C-2). ESI-MS, m/z (Rel. Int.): 380 (M + H+, 100).
6-(4-Chlorobenzyl)-5-ethyl-2-[2-(morpholin-4-yl)ethyl]thiopyrimidin-4(3H)-one (6d) White solid.
1
M.p.: 133–135 °C. Yield: 0.271 g (69%). H-NMR (DMSO-d6): δ = 0.94 (t, 3H, J = 7.5 Hz, CH3),
2.31 (t, 4H, J = 4.5 Hz, 2 × CH2), 2.43–2.46 (m, 4H, 2 × CH2), 3.12 (t, 2H, J = 7.0 Hz, CH2), 3.53 (t, 4H,
J = 4.5 Hz, CH2), 3.85 (s, 2H, CH2), 7.25, 7.33 (2 × d, 4H, J = 8.5 Hz, Harom.), 12.79 (s, 1H, NH).
13C-NMR (DMSO-d6): δ = 13.16 (CH3), 18.02 (CH2), 26.64 (CH2), 30.59 (CH2), 52.82, 65.96
(Cmorpholin.), 57.32 (CH2), 121.27 (C-5), 128.09, 130.64, 130.78, 137.55 (Carom.), 157.20 (C-6), 159.44
(C-4), 162.77 (C-4). ESI-MS, m/z (Rel. Int.): 394 (M + H+, 100).
5-Ethyl-6-(4-methylbenzyl)-2-[2-(morpholin-4-yl)ethyl]thiopyrimidin-4(3H)-one (6e) White solid.
1
M.p.: 137–139 °C.Yield: 0.236 g (63%). H-NMR (DMSO-d6): δ = 0.90 (t, 3H, J = 7.5 Hz, CH3),
2.25 (s, 3H, CH3), 2.31–2.39 (m, 6H, 3 × CH2), 2.58 (t, 2H, J = 7.0 Hz, CH2), 3.15 (t, 2H, J = 7.0 Hz, CH2),
3.51 (t, 4H, J = 4.5 Hz, 2 × CH2), 3.79 (s, 2H, CH2), 7.07, 7.11 (2 × d, 4H, J = 8.0 Hz, Harom.),
12.49 (s, 1H, NH). 13C-NMR (DMSO-d6): δ = 13.14 (CH3), 18.08 (CH2), 20.51 (CH3), 26.62 (CH2),
52.83, 65.98 (Cmorpholin.), 57.38 (CH2), 120.98 (C-5), 128.56, 128.76, 135.04, 135.41 (Carom.),
157.93 (C-6), 162.20 (C-4), 164.63 (C-2). ESI-MS, m/z (Rel. Int.): 374 (M + H+, 100).
6-(3,4-Dimethoxybenzyl)-5-ethyl-2-[2-(morpholin-4-yl)ethyl]thiopyrimidin-4(3H)-one (6f) White solid.
1
M.p.: 151–152 °C, Yield: 0.276 g (66%). H-NMR (DMSO-d6): δ = 0.90 (t, 3H, J = 7.5 Hz, CH3),
2.30–2.39 (m, 6H, 3 × CH2), 2.58 (t, 2H, J = 7.0 Hz, CH2), 3.21 (t, 2H, J = 7.0 Hz, CH2), 3.57 (t, 4H,
J = 4.5 Hz, 2 × CH2), 3.70 (s, 3H, OCH3), 3.72 (s, 3H, OCH3), 3.76 (s, 2H, CH2), 6.72–6.87 (m, 3H,
13
H
arom.), 12.54 (s, 1H, NH). C-NMR (DMSO-d6): δ = 13.32 (CH3), 18.06 (CH2), 26.68 (CH2), 52.83,
65.98 (Cmorpholin.), 55.36 (OCH3), 55.42 (OCH3), 57.44 (CH2), 117.23 (C-5), 111.76, 112.85, 120.57,