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HETEROCYCLES, Vol. 75, No. 12, 2008
3-(4-Chlorophenyl)thieno[2,3-e][1,2,4]triazolo[4,3-c]pyrimidine (10b):
77% Yield, mp 264 – 265 °C; 1H NMR (CDCl3): δ 9.02 (s, 1H, H-5), 7.87 - 7.79 (m, 3H, H-8, H-3’ and
H-5’), 7.65 - 7.60(m, 3H, H-7, H-2’ and H-6’); MS: (m/z) 286 (M+), 134. Anal. Calcd for C13H7ClN4S: C,
54.45; H, 2.46, N, 19.54. Found: C, 54.29; H, 2.41; N, 19.68.
3-p-Tolylthieno[2,3-e][1,2,4]triazolo[4,3-c]pyrimidine (10c):
70% Yield, mp 206 – 208 °C; 1H NMR (CDCl3): δ 9.20 (s, 1H, H-5), 8.23 (m, 2H, H-2’ and H-6’), 7.86(d,
J = 5.9 Hz, 1H, H-8), 7.63 (d, J = 6.0 Hz, 1H, H-7), 7.35 (m, 2H, H-3’and H-5’); MS: (m/z) 266 (M+),
131, 91. Anal. Calcd for C14H10N4S: C, 63.14; H, 3.78, N, 21.04. Found: C, 62.85; H, 3.71; N, 21.35.
3-(4-Methoxyphenyl)thieno[2,3-e][1,2,4]triazolo[4,3-c]pyrimidine (10d):
70% Yield, mp 142 – 143 °C; 1H NMR (CDCl3): δ 9.29 (s, 1H, H-5), 8.25 (m, 2H, H-2’ and H-6’), 7.87
(d, J = 5.9 Hz, 1H, H-8), 7.64 (d, J = 6.0 Hz, 1H, H-7), 7.05 (m, 2H, H-3’and H-5’), 3.90 (s, 3H, methyl);
MS: (m/z) 282 (M+), 132. Anal. Calcd for C14H10N4OS: C, 59.56; H, 3.57, N, 19.85. Found: C, 60.20; H,
3.68; N, 20.22.
3-(4-Bromophenyl)thieno[2,3-e][1,2,4]triazolo[4,3-c]pyrimidine (10e):
78% Yield, mp 168 – 169 °C; 1H NMR (CDCl3): δ 9.01 (s, 1H, H-5), 7.96 (d, J = 6.0 Hz, 1H, H-8), 7.75 -
7.66 (m, 4H, H-2’, H-3’, H-5’ and H-6’), 7.65 (d, J = 6.0 Hz, 1H, H-7); MS: (m/z) 331 (M+). Anal. Calcd
for C13H7BrN4S: C, 47.15; H, 2.13, N, 16.92. Found: C, 46.84; H, 2.29; N, 17.26.
3-(3-Chlorophenyl)thieno[2,3-e][1,2,4]triazolo[4,3-c]pyrimidine (10f):
81% Yield, mp 158 – 159 °C; 1H NMR (CDCl3): δ 9.04 (s, 1H, H-5), 7.91 (d, J = 6.0 Hz, 1H, H-8), 7.81
(s, 1H, H-2’), 7.75 - 7.72 (m, 2H, H-7, H-4’), 7.62 - 7.59 (m, 2H, H-5’ and H-6’); MS: (m/z) 286 (M+).
Anal. Calcd for C13H7ClN4S: C, 54.45; H, 2.46, N, 19.54. Found: C, 54.63; H, 2.30; N, 19.30.
3-m-Tolylthieno[2,3-e][1,2,4]triazolo[4,3-c]pyrimidine (10g):
72% Yield, mp 274 – 276 °C; 1H NMR (CDCl3): δ 9.06 (s, 1H, H-5), 7.79 (d, J = 6.0 Hz, 1H, H-8), 7.72
(s, 1H, H-2’), 7.67 (d, 1H, H-6’), 7.62 (d, J = 6.0 Hz, 1H, H-7), 7.55 (t, 1H, H-5’), 7.44 (d, 1H, H-4’);
MS: (m/z) 266 (M+), 149, 132. Anal. Calcd for C14H10N4S: C, 63.14; H, 3.78, N, 21.04. Found: C, 63.43;
H, 3.60; N, 21.33.
3-(3-Bromophenyl)thieno[2,3-e][1,2,4]triazolo[4,3-c]pyrimidine (10h):
77% Yield, mp 186 – 187 °C; 1H NMR (CDCl3): δ 8.98 (s, 1H, H-5), 8.05 (s, 1H, H-2’) 7.95 (d, J = 6.0
Hz, 1H, H-8), 7.86 - 7.79 (m, 3H, H-9, H-4’ and H-6’), 7.59 (t, 1H, H-5’); MS: (m/z) 331 (M+). Anal.
Calcd for C13H7BrN4S: C, 47.15; H, 2.13, N, 16.92. Found: C, 46.94; H, 1.91; N, 17.10.
3-(2-Methoxyphenyl)thieno[2,3-e][1,2,4]triazolo[4,3-c]pyrimidine (10i):
70% Yield, mp 191 – 192 °C; 1H NMR (CDCl3): δ 9.00 (s, 1H, H-5), 7.94 (d, J = 6.0 Hz, 1H, H-8), 7.75
(d, J = 5.9 Hz, 1H, H-9), 7.68 - 7.57 (m, 2H, H-4’and H-6’), 7.52 (t, 1H, H-4’) 7.46 (d, 1H, H-3’), 2.52 (s,