46 JOURNAL OF CHEMICAL RESEARCH 2016
listed. The 1H NMR (300 MHz) and the 13C NMR (75 MHz) spectra were
recorded on a Bruker Avance DRX-400 Fourier transformer spectrometer.
Chemical shifts are reported in ppm downfield from TMS as an internal
standard. The mass spectra were recorded on a Varian Mat CH-7 at 70 eV.
Elemental analyses were performed on a Thermo Finnigan Flash EA 1112
microanalyser.
210–212 °C; IR (KBr disc) (νmax cm–1): 3396 3444, 2850, 1347; 1H NMR
(300 MHz, CDCl3): δ 1.21 (t, J = 5.3 Hz, 3H, CH3), 2.31 (s, 3H, CH3), 3.23
(q, J = 5.3 Hz, 2H, CH2N), 3.27 (t, J = 6.3 Hz, 4H, CH2N), 3.66 (t, J = 6.3
Hz, 4H, CH2N), 6.48 (d, J = 5.8 Hz, 1H, ArH), 6.52 (d, J = 5.8 Hz, 1H,
ArH), 8.36 (br s, 1H, NH, D2O exchangeable); 13C NMR (75 MHz, CDCl3):
δ 22.1, 24.5, 43.2, 46.5, 54.1, 120.9, 142.7, 142.9, 143.8, 144.6, 145.9, 151.2,
153.7; MS (m/z): 346 (M+), 348 (M+ + 2). Anal. calcd for C15H19ClN8: C,
51.95; H, 5.52; N, 32.31; found: C, 51.89; H, 5.47; N, 32.25%.
Synthesis of 2,8-dichloro-10-methyl-6H-pyridazino[6,1-c]pyrimido-
[5,4-e][1,2,4]triazine 3: general procedure
A solution of compound 1 (0.14 g, 1 mmol) and 5-bromo-2,4-dichloro-6-
methylpyrimidine (2) (0.24 g, 1 mmol) in pyridine (5 mL) was stirred
at room temperature for 1 h. After the completion of the reaction which
was monitored by TLC using CHCl3:MeOH (9:1), the resulting solid was
filtered off, washed with water (2 × 10 mL) and recrystallised from EtOH
to give the product as an orange powder; yield 65%; m.p. 185 °C; IR (KBr
disc) (νmax cm–1): 3394, 3023, 2920, 2836, 1643, 833; 1H NMR (400 MHz,
DMSO-d6): δ 2.36 (s, 3H, CH3), 7.17 (d, 1H, ArH), 7.85 (d, 1H, ArH), 8.91
(s, 1H, NH, D2O exchangeable); 13C NMR (100 MHz, DMSO-d6): δ 23.7,
114.6, 115.4, 120.9, 125.5, 127.1, 129.9, 143.1, 145.0; MS (m/z): 268 (M+),
270 (M+ + 2), 272 (M+ + 4). Anal. calcd for C9H6Cl2N6: C, 40.17; H, 2.25; N,
31.23; found: C, 40.01; H, 2.20; N, 31.17%.
The authors gratefully acknowledge the Research Council of the
Ferdowsi University of Mashhad for financial support of this project
(3/31474).
Received 26 September 2015; accepted 7 December 2015
Published online 1 January 2016
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205–206 °C; IR (KBr disc) (νmax cm–1): 3417, 2918, 2849, 799; H NMR
(300 MHz, CDCl3): δ 2.35 (s, 3H, CH3), 3.66 (m, 4H, CH2N), 3.81 (m, 4H,
CH2O), 6.52 (d, J = 5.8 Hz, 1H, ArH), 6.59 (d, J = 5.8 Hz, 1H, ArH), 8.59
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30.66; found: C, 48.77; H, 4.38; N, 30.57%.
2-Chloro-10-methyl-8-(piperidin-1-yl)-6H-pyridazino[6,1-c]
pyrimido[5,4-e][1,2,4]triazine (4c): Light yellow powder; yield 65%;
m.p. 206–207 °C; IR (KBr disc) (νmax cm–1): 3212, 2953, 2924, 2852, 1640;
1H NMR (300 MHz, CDCl3): δ 1.52 (m, 4H, CH2), 1.61 (m, 2H, CH2), 2.33
(s, 3H, CH3), 3.69 (t, J = 6.3 Hz, 4H, CH2N), 6.53 (d, J = 5.8 Hz, 1H, ArH),
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calcd for C14H16ClN7: C, 52.91; H, 5.07; N, 30.85; found: C, 52.83; H, 4.98;
N, 30.75%.
2-Chloro-10-methyl-8-(4-methylpiperazin-1-yl)-6H-pyridazino[6,1-c]
pyrimido[5,4-e][1,2,4]triazine (4d): Brown powder; yield 66%; m.p.
220–222 °C; IR (KBr disc) (νmax cm–1): 3395, 3143, 2918, 2849; 1H NMR
(300 MHz, CDCl3): δ 2.30 (s, 3H, CH3), 2.72 (s, 3H, CH3N), 3.29 (t, J =
6.3 Hz, 4H, CH2N), 3.69 (t, J = 6.3 Hz, 4H, CH2N), 6.49 (d, J = 5.8
Hz, 1H, ArH), 6.54 (d, J = 5.8 Hz, 1H, ArH), 8.02 (br s, 1H, NH, D2O
exchangeable); 13C NMR (75 MHz, CDCl3): δ 24.5, 43.7, 46.2, 54.9, 120.0,
142.0, 142.0, 143.1, 144.1, 145.0, 150.0, 153.0; MS (m/z): 332 (M+), 334
(M+ + 2). Anal. calcd for C14H17ClN8: C, 50.53; H, 5.15; N, 33.67; found: C,
50.45; H, 5.04; N, 33.58%.
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