Page 171 - 《精细化工》2022年第12期

第 12 期 刘 波，等: 噻吩并[2,3-d]嘧啶类衍生物的合成及抗肿瘤活性 ·2537·

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(s, 3H, 6-CH 3), 2.49(s, 3H, 5-CH 3); CNMR 〔100 MHz, 152 ℃; HNMR 〔400 MHz, (CD 3) 2CO〕, δ: 7.42 (s, 1H,
(CD 3) 2CO〕, δ: 164.0, 157.4, 149.9, 142.1, 132.5, 131.0, NH), 7.39~7.13 (m, 4H, Ar—H), 4.86 (s, 2H, Ar—CH 2),
130.2, 129.9, 127.0, 124.6, 121.8, 121.6, 117.8, 43.8, 2.60 (3H, 6-CH 3), 2.49 (s, 3H, 5-CH 3),2.43 (s, H, Ar—
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13.3, 12.6; IR (KBr), v/cm : 3451 (N—H), 1589 (C==N), CH 3); CNMR 〔100 MHz, (CD 3) 2CO〕, δ: 163.9, 157.6,
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1336, 1197 (CF 3); EI-MS (M ), m/Z，实测值（计算值）： 150.4, 150.0, 136.7, 135.9, 132.4, 128.0, 127.0, 124.6,
415.19 (415.00); 元素分析，C 16H 13BrF 3N 3S, 实验值 121.6, 118.9, 117.8, 42.2, 18.3, 13.3, 12.5; IR (KBr),
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（计算值）：w(C) = 46.22% (46.17%), w(H) = 3.31% v/cm : 3500 (N—H), 1587 (C==N), 1334, 1180 (CF 3);
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(3.15%), w(N) = 10.04% (10.09%)。 EI-MS (M ), m/Z，实测值（计算值）：351.27 (351.10);
5,6-二甲基-2-三氟甲基-4-(2-溴苄氨基)噻吩并 元素分析，C 17H 16F 3N 3S, 实验值（计算值）：w(C) =
58.25% (58.11%), w(H) = 4.84% (4.59%), w(N) =
[2,3-d]嘧啶（Ⅲj）：白色固体，收率 84%, m.p. 127~
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128 ℃; HNMR 〔400 MHz, (CD 3) 2CO〕, δ: 7.63 (s, 1H, 12.20% (11.96%)。
5,6-二甲基-2-三氟甲基-4-(4-甲氧基苄氨基)噻吩
NH), 7.56~7.21 (m, 4H, Ar—H), 4.93 (s, 2H, Ar—CH 2),
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2.65 (s, 3H, 6-CH 3), 2.51 (s, 3H, 5-CH 3); CNMR 〔100 并[2,3-d]嘧啶（Ⅲn）：白色固体，收率 79%, m.p. 133~
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134 ℃; HNMR 〔400 MHz, (CD 3) 2CO〕, δ: 7.42 (s, 1H,
MHz, (CD 3) 2CO〕, δ: 164.0, 157.5, 150.3, 137.7, 132.8,
132.6 130.9, 128.9, 127.5, 124.5, 122.9, 121.6, 117.9, NH), 7.40~6.86 (m, 4H, Ar—H), 4.79 (s, 2H, Ar—CH 2),
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44.9, 13.3, 12.6; IR (KBr), v/cm : 3479 (N—H), 1587 3.76 (3H, OCH 3), 2.56 (s, 3H, 6-CH 3), 2.47 (s, 3H,
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(C==N), 1330, 1197 (CF 3); EI-MS (M ), m/Z，实测值（计 5-CH 3 ); CNMR 〔100 MHz, (CD 3 ) 2CO〕, δ: 163.9, 159.0,
157.5, 150.0, 132.3, 131.1, 129.3, 124.5, 121.7, 119.0,
算值）：415.19 (415.00); 元素分析，C 16H 13BrF 3N 3S，
117.7, 116.2, 113.7, 54.6, 44.0, 13.3, 12.5; IR (KBr),
实验值（计算值）：w(C) = 46.43% (46.17%), w(H) = v/cm : 3506 (N—H), 1587 (C==N), 1332, 1185 (CF 3);
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3.26% (3.15%), w(N) = 10.22% (10.09%)。 EI-MS (M ), m/Z，实测值（计算值）：367.28 (367.10);
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5,6-二甲基-2-三氟甲基-4-(4-甲基苄氨基)噻吩并 元素分析，C 17H 16F 3N 3OS, 实验值（计算值）：w(C) =
[2,3-d]嘧啶（Ⅲk）：白色固体，收率 79%, m.p. 132~ 55.41% (55.58%), w(H) = 4.44% (4.39%), w(N) =
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133 ℃; HNMR 〔400 MHz, (CD 3) 2CO〕, δ: 7.37 (s, 1H, 11.51% (11.44%)。
NH), 7.28~7.12 (m, 4H, Ar—H), 4.82 (s, 2H, Ar—CH 2), 5,6-二甲基-2-三氟甲基-4-(3-甲氧基苄氨基)噻吩
2.57 (3H, 6-CH 3), 2.48 (s, 3H, 5-CH 3), 2.28 (s, 3H, Ar— 并[2,3-d]嘧啶（Ⅲo）：白色固体，收率 81%, m.p. 116~
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CH 3); CNMR 〔100 MHz, (CD 3) 2CO〕, δ: 163.9, 157.6, 117 ℃; HNMR 〔400 MHz, (CD 3) 2CO〕, δ: 7.26 (s, 1H,
150.4, 150.0, 136.4, 136.2, 132.3, 128.9, 127.9, 124.6, NH), 7.24~7.04 (m, 4H, Ar—H), 4.86 (s, 2H, Ar—CH 2),
121.7, 118.9, 117.7, 44.1, 20.2, 13.3, 12.5; IR (KBr), 3.78 (s, 3H, OCH 3), 2.60 (s, 3H, 6-CH 3), 2.50 (s, 3H,
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v/cm : 3473 (N—H), 1589 (C==N), 1334, 1180 (CF 3); 5-CH 3 ); CNMR 〔100 MHz, (CD 3 ) 2CO〕, δ: 163.9, 159.9,
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EI-MS (M ), m/Z，实测值（计算值）：351.28 (351.10); 157.6, 150.0, 140.8, 132.4, 129.3, 124.6, 121.7, 120.05,
元素分析，C 17H 16F 3N 3S，实验值（计算值）：w(C) = 117.8, 113.5, 112.5, 54.5, 44.3, 13.3, 12.5; IR (KBr),
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57.97% (58.11%), w(H) = 4.53% (4.59%), w(N) = v/cm : 3495 (N—H), 1577 (C==N), 1342, 1185 (CF 3);
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12.06% (11.96%)。 EI-MS (M ), m/Z，实测值（计算值）：367.28 (367.10);
5,6-二甲基-2-三氟甲基-4-(3-甲基苄氨基)噻吩并 元素分析，C 17H 16F 3N 3OS, 实验值（计算值）：w(C) =
[2,3-d]嘧啶（Ⅲl）：白色固体，收率 82%, m.p. 101~ 55.71% (55.58%), w(H) = 4.48% (4.39%), w(N) =
11.42% (11.44%)。
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102 ℃; HNMR 〔400 MHz, (CD 3) 2CO〕, δ: 7.31 (s, 1H,
5,6-二甲基-2-三氟甲基-4-(2-甲氧基苄氨基)噻吩
NH), 7.28~7.05 (m, 4H, Ar—H), 4.83 (s, 2H, Ar—CH 2),
并[2,3-d]嘧啶（Ⅲp）：白色固体，收率 88%, m.p. 158~
2.58 (3H, 6-CH 3), 2.48(s, 3H, 5-CH 3), 2.29 (s, 3H, Ar— 1
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CH 3); IR (KBr), v/cm : 3471 (N—H), 1583 (C==N), 159 ℃; HNMR 〔400 MHz, (CD 3) 2CO〕, δ: 7.38 (s, 1H,
NH), 7.29~6.88 (m, 4H, Ar—H), 4.85 (s, 2H, Ar—CH 2),
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1332, 1183 (CF 3); CNMR 〔100 MHz, (CD 3) 2CO〕, δ: 3.94 (s, 3H, OCH 3), 2.59 (s, 3H, 6-CH 3), 2.48 (s, 3H,
163.9, 157.6, 150.0, 139.1, 137.7, 132.3, 128.7, 128.2, 5-CH 3); CNMR 〔100 MHz, (CD 3) 2CO〕, δ: 163.7,
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127.7, 125.0, 124.6, 121.7, 117.7, 144.3, 20.5,13.3, 12.5;
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EI-MS (M ), m/Z，实测值（计算值）：351.28 (351.10); 157.7, 150.4, 132.4, 129.2, 128.6, 126.3, 124.4, 121.6,
120.3, 117.8 , 116.2, 110.5, 54.9, 40.4, 13.1, 12.5; IR
元素分析，C 17H 16F 3N 3S, 实验值（计算值）：w(C) = (KBr), v/cm : 3530 (N—H), 1577 (C==N), 1330, 1187
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57.89% (58.11%), w(H) = 4.43% (4.59%), w(N) = (CF 3); EI-MS (M ), m/Z，实测值（计算值）：367.28
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12.12% (11.96%)。 (367.10); 元素分析，C 17H 16F 3N 3OS, 实验值（计算值）:
5,6-二甲基-2-三氟甲基-4-(2-甲基苄氨基)噻吩并 w(C) = 55.61% (55.58%), w(H) = 4.12% (4.39%), w(N) =
[2,3-d]嘧啶（Ⅲm）：白色固体，收率 86%, m.p. 151~ 11. 24% (11.44%)。