Molecules 2010, 15
1979
2-Methyl-N-(2-(2-(4-methylpiperazino)pyrimidin-4-yl)ethyl)propan-2-amine (7). This compound was
obtained as an oil in 38% yield; 1H NMR (CDCl3): δ 8.20 (d, J = 4.8 Hz, 1H), 6.40 (d, J = 5.0 Hz, 1H),
3.85 (t, J = 3.2 Hz, 4H), 2.97–2.92 (m, 2H), 2.79–2.75 (m, 2H), 2.48 (t, J = 5.0 Hz, 4H), 2.34 (s, 3H),
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1.11 (s, 9H); C NMR (CDCl3): δ 169.5, 161.6, 157.4, 109.4, 55.0, 50.2, 46.2, 43.6, 40.8, 38.4, 29.0.
High-resolution MS (ESI, positive ion mode): calcd. for C15H26 N5 (M+ + 1), m/z 278.2345; found m/z
278.23.
N-Benzyl-2-(2-(4-methylpiperazino)pyrimidin-4-yl)ethanamine tetrahydrobromide (8). This salt was
obtained in 62% yield; m.p. 110–112 °C; 1H-NMR (DMSO-d6): δ 10.0 (bs, 1H), 8.96 (bs, 1H), 8.37 (d,
J = 4.8 Hz, 1H), 7.58–7.55 (m, 2H), 7.49–7.42 (m, 3H), 6.73 (d, J = 5.4 Hz, 1H), 4.68 (d, J = 14.4 Hz,
2H), 4.24 (t, J = 5.4 Hz, 2H), 3.55–3.50 (m, 2H), 3.39–3.29 (m, 4H), 3.06 (t, J = 7.6 Hz, 4H), 2.86 (bs,
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3H); C-NMR (CDCl3): δ 171.3, 163.2, 158.3, 143.2, 128.3, 128.1, 125.9, 110.2, 55.3, 54.2, 46.3,
44.0, 39.3, 34.2. MS (ESI) m/z 312 (M+ + H). Anal. Calcd for C18H25N5·4HBr·H2O: C, 33.10; H, 4.78;
N, 10.72. Found: C, 33.43; H, 5.10; N, 10.66.
4-(2-Methoxyethyl)-2-4-methylpiperazino)pyrimidine trihydrobromide (9). The free base was obtained
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as an oil in 55% yield; H-NMR for the free base (CDCl3): δ 8.22 (d, J = 5.0 Hz, 1H), 6.44 (d,
J = 5.0 Hz, 1H), 3.87 (t, J = 5.0 Hz, 4H), 3.77 (t, J = 6.8 Hz, 2H), 3.37 (s, 3H), 2.85 (t, J = 6.8 Hz,
2H), 2.48 (t, J = 4.8 Hz, 4H), 2.36 (s, 3H); 13C-NMR (CDCl3): δ 168.1, 161.7, 157.4, 109.4, 58.7, 55.0,
46.2, 43.6, 38.0, 29.7. High-resolution MS for the free base (ESI, positive ion mode): calcd. for C12H20
N4O (M+ + 1), m/z 237.1705; found m/z 237.1715. Anal. calcd for: calcd for C12H20N4O·3HBr: C,
30.09; H, 4.24; N, 11.70. Found: C, 29.86; H, 4.34; N, 12.12.
4-(2-(Ethylthio)ethyl)-2-(4-methylpiperazino)pyrimidine (10). This compound was obtained as an oil in
25% yield; 1H-NMR (CDCl3): δ 8.22 (d, J = 5.0 Hz, 1H), 6.41 (d, J = 5.0 Hz, 1H), 3.87 (t, J = 4.8 Hz,
4H), 2.92–2.90 (m, 2H), 2.88–2.86 (m, 2H), 2.60 (q, J = 7.4 Hz, 2H), 2.49 (t, J = 4.8 Hz, 4H), 2.36 (s,
3H), 1.29 (t, J = 7.4 Hz, 3H); 13C-NMR (CDCl3): δ 168.9, 161.7, 157.4, 109.1, 55.0, 46.2, 43.6, 38.0,
29.8, 26.0, 14.7. High-resolution MS (ESI, positive ion mode): calcd. for C13H22N4S (M+ + 1), m/z
267.1632; found m/z 267.1643.
N-Benzyl-2-(2-(4-methylpiperazino)pyrimidin-4-yl)-2-phenylethanamine (11). This compound was
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obtained as an oil in 57% yield; H-NMR (CDCl3) δ 8.13 (d, J = 5.1 Hz, 1H), 7.25 (m, 10H), 6.29
(d, J = 5.1 Hz, 1H), 4.11 (dd, J = 6.4, 8.4Hz, 1H), 3.82 (m, 6H), 3.49 (dd, J = 8.4, 11.8Hz, 1H), 3.07
(dd, J = 6.4, 11.8Hz, 1H), 2.45 (m, 4H), 2.34 (s, 3H); 13C-NMR (CDCl3) δ 170.8, 161.6, 157.7, 141.1,
140.3, 128.6, 128.4, 128.3, 128.1, 127.0, 126.9, 109.7, 55.0, 53.9, 53.1, 53.0, 46.3, 43.7. High
resolution MS (ESI, positive ion mode): calcd. for C24H29N5, (M++1), m/z 388.2501, found m/z
388.2491.
4-(2-Ethylthio)-1-phenylethyl)-2-(4-methylpiperazino)pyrimidine (12). This compound was obtained
as an oil in 37% yield; 1H-NMR (CDCl3) δ 8.15 (d, J = 5.2 Hz, 1H), 7.29 (m, 5H), 6.34 (d, J = 5.2 Hz,
1H), 4.01 (m, 1H), 3.88 (m, 4H), 3.48 (m, 1H), 3.06 (m, 1H), 2.48 (m, 6H), 2.35 (s, 3H), 1.22 (t,
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J = 7.2 Hz, 3H); C-NMR (CDCl3): δ 170.7, 161.6, 157.7, 141.7, 128.5, 128.1, 127.1, 109.4, 55.0,