2354
A. Shockravi, M. Sadeghpour, and A. Olyaei
H-4,6), 8.32 (d, 2H, J ¼ 4.8 Hz, pyrimidine H-40,60), 9.34 (broad, 2H, OH)
1
ppm; H NMR (500 MHz, CDCl3 þ D2O): d ¼ 2.15 (s, 6H, CH3), 6.54
(s, 2H, methine-H), 6.55–6.58 (m, 2H, pyrimidine H-5,50), 6.91 (s,1H,
phenolic H-4), 6.92 (s,1H, phenolic H-40), 7.01 (s, 2H, phenolic H-6,60),
7.29–7.38 (m, 10H, ph-H), 8.29 (d, 2H, J ¼ 4.8 Hz, pyrimidine H-4,6),
8.31 (d, 2H, J ¼ 4.8 Hz, pyrimidine H-40,60) ppm; 13C NMR (125 MHz,
CDCl3): d ¼ 20.98, 54.28, 111.52, 111.53, 121.71, 127.20, 127.22, 127.54,
128.85, 129.76, 130.67, 130.68, 130.73, 130.74, 133.60, 141.53, 141.55,
152.54, 158.54, 161.78 ppm; MS: m=z (%) ¼ 612 [M]þ, 611 [Mꢁ1]þ,
583, 527, 489, 377, 333, 262, 195, 183, 95. Anal. calcd. for C36H32N6O2S:
C, 70.58; H, 5.22, N, 13.72. Found: C, 70.52; H, 5.28; N, 13.77.
Thio-bis-[5-methyl-3-(4-methylphenyl(2-pyrimidinyl
amino)methyl)-2-phenol (3b)
Pale yellow crystal; IR (KBr): 3410, 3275, 3022, 2920, 1588, 1513, 1448,
1234, 801 cmꢁ1; 1H NMR (500 MHz, CDCl3): d ¼ 2.15 (s, 6H, CH3), 2.36
(s, 6H, CH3), 6.53–6.55 (m, 6H, NH, methine-H, pyrimidine H-5,50), 6.92
(s, 1H, phenolic H-4), 6.93 (s, 1H, phenolic H-40), 7.00 (s, 2H, phenolic
H-6,60), 7.15–7.30 (m, 8H, tolyl-H), 8.25 (d, 2H, J ¼ 4.8 Hz, pyrimidine
H-4,6), 8.27 (d, 2H, J ¼ 4.8 Hz, pyrimidine H-40,60), 9.35 (broad, 2H,
OH) ppm; 13C NMR (125 MHz, CDCl3): d ¼ 20.99, 21.74, 54.01,
111.35, 111.37, 121.70, 121.72, 127.18, 127.19, 129.55, 129.96, 130.53,
130.57, 130.65, 130.67, 133.43, 133.46, 137.13, 138.56, 138.58, 152.52,
152.56, 158.51, 161.78 ppm; MS: m=z (%) ¼ 640 [M]þ, 554, 454, 350,
244, 212, 197, 152, 120, 105, 91. Anal. calcd. for C38H36N6O2S: C,
71.25; H, 5.62; N, 13.12. Found: C, 71.30; H, 5.55; N, 13.10.
Thio-bis-[5-methyl-3-(4-methoxyphenyl(2-pyrimidinyl
amino)methyl)-2-phenol (3c)
Pale yellow crystal; IR (KBr): 3410, 3278, 3002, 2931, 1587, 1512, 1454,
1248, 1177, 801 cmꢁ1
;
1H NMR (500 MHz, CDCl3): d ¼ 2.16 (s, 6H,
CH3), 3.82 (s, 6H, OCH3), 6.43–6.57 (m, 6H, NH, methine-H, pyrimidine
H-5,50), 6.84–7.30 (m, 12H, phenolic H-4,40,6,60, OMe-ph-H), 8.25 (d, 2H,
J ¼ 4.8 Hz, pyrimidine H-4,6), 8.28 (d, 2H, J ¼ 4.8 Hz, pyrimidine H-40,60),
9.34 (broad, 2H, OH) ppm; 13C NMR (125 MHz, CDCl3): d ¼ 21.00, 53.76,
55.67, 111.40, 111.42, 114.22, 114.29, 121.70, 121.72, 128.39, 128.41,
129.98, 130.52, 130.54, 130.65, 130.67, 133.50, 133.61, 133.63, 152.50,
152.53, 158.51, 159.04, 161.74 ppm; MS: m=z (%) ¼ 672 [M]þ, 615, 602,
574, 500, 486, 366, 260, 213, 152, 135, 95. Anal. calcd. for C38H36N6O4S:
C, 67.85; H, 5.35; N, 12.50. Found: C, 67.90; H, 5.26; N, 12.59.