Synthesis of 1,2,9-trisubstituted purin-6(9H)-ones
Anal. calcd for C14H14N4O2: C, 62.21; H, 5.22; N, 20.73. Found: C, 62.14; H, 5.35;
N, 20.66 %.
2-(2-Methoxyphenyl)-1,9-dimethyl-1H-purin-6(9H)-one (e)
White crystals; m.p. 251–252 °C; IR (KBr, m, cm-1): 3316, 2928, 1678 (C=O),
1556, 1474, 1346 cm-1; 1H NMR (300 MHz, CDCl3) (d, ppm): 2.73 (3H, s, CH3),
3.62 (3H, s, CH3), 3.74 (3H, s, OCH3), 7.02 (1H, d, J = 7.2 Hz, ArH), 7.09 (1H, d,
J = 7.2 Hz, ArH), 7.38 (1H, t, J = 7.2 Hz, ArH), 7.77 (1H, d, J = 7.2 Hz, ArH),
7.91 (1H, s, imidazole-H); ESI-MS m/z: 271.19 (M ? H)?. Anal. calcd for
C14H14N4O2: C, 62.21; H, 5.22; N, 20.73. Found: C, 62.18; H, 5.31; N, 20.67 %.
2-(4-Chlorophenyl)-1,9-dimethyl-1H-purin-6(9H)-one (f)
White crystals; m.p. 276–277 °C; IR (KBr, m, cm-1): 3325, 2928, 1678 (C=O),
1555, 1416, 1371 cm-1; 1H NMR (300 MHz, CDCl3) (d, ppm): 2.74 (3H, s, CH3),
3.65 (3H, s, CH3), 7.52 (2H, d, J = 7.2 Hz, ArH), 7.79 (2H, d, J = 7.2 Hz, ArH),
7.95 (1H, s, imidazole-H); ESI-MS m/z: 275.33 (M ? H)?. Anal. calcd for
C13H11N4OCl: C, 56.84; H, 4.04; N, 20.40. Found: C, 56.72; H, 4.15; N, 20.27 %.
2-(2,4-Dichlorophenyl)-1,9-dimethyl-1H-purin-6(9H)-one (g)
White crystals; m.p. [300 °C; IR (KBr, m, cm-1): 3325, 2928, 1672 (C=O), 1559,
1
1474, 1324 cm-1; H NMR (300 MHz, CDCl3) (d, ppm): 2.74 (3H, s, CH3), 3.63
(3H, s, CH3), 7.32 (1H, d, J = 7.2 Hz, ArH), 7.51 (1H, s, ArH), 7.78 (1H, d,
J = 7.2 Hz, ArH), 7.95 (1H, s, imidazole-H); ESI-MS m/z: 309.07 (M ? H)?.
Anal. calcd for C13H10N4OCl2: C, 50.51; H, 3.26; N, 18.12. Found: C, 50.43; H,
3.19; N, 18.28 %.
2-(2-Fluorophenyl)-1,9-dimethyl-1H-purin-6(9H)-one (h)
White crystals; m.p. 265–266 °C; IR (KBr, m, cm-1): 3302, 2931, 1685 (C=O),
1514, 1426, 1332 cm-1; 1H NMR (300 MHz, CDCl3) (d, ppm): 2.74 (3H, s, CH3),
3.63 (3H, s, CH3), 7.22 (1H, d, J = 7.2 Hz, ArH), 7.30 (1H, t, J = 7.2 Hz, ArH),
7.45 (1H, t, J = 7.2 Hz, ArH), 7.88 (1H, d, J = 7.2 Hz, ArH), 7.96 (1H, s,
imidazole-H); ESI-MS m/z: 259.09 (M ? H)?. Anal. calcd for C13H11N4OF: C,
60.46; H, 4.29; N, 21.69. Found: C, 60.49; H, 4.16; N, 21.75 %.
2-(4-Fluorophenyl)-1,9-dimethyl-1H-purin-6(9H)-one (i)
White crystals; m.p. 241–242 °C; IR (KBr, m, cm-1): 3321, 2928, 1678 (C=O),
1551, 1414, 1363 cm-1; 1H NMR (300 MHz, CDCl3) (d, ppm): 2.74 (3H, s, CH3),
3.64 (3H, s, CH3), 7.20 (2H, d, J = 7.2 Hz, ArH), 7.89 (2H, d, J = 7.2 Hz, ArH),
7.97 (1H, s, imidazole-H); ESI-MS m/z: 259.03 (M ? H)?. Anal. calcd for
C13H11N4OF: C, 60.46; H, 4.29; N, 21.69. Found: C, 60.53; H, 4.21; N, 21.77 %.
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