Chemical Papers
4‑Fluoro‑N‑(4‑((2‑methyl‑6‑(trifuoromethyl)pyrimidin‑4‑yl)
oxy)phenyl)‑3‑nitrobenzamide (4u) White crystals; yield
10.64 (s, 1H, –CONH–), 7.88 (d, 1H, J= 8.55 Hz, Ph-H),
7.79 (d, 2H, J = 9.2 Hz, Ph-H), 7.74 (m, 1H, Ph-H), 7.50
(s, 1H, pyrimidine-H), 7.46 (dd, 1H, J1 = 2.3 Hz, J2 =
8.6 Hz, Ph-H), 7.28 (d, 2H, J=9.15 Hz, Ph-H), 2.52(s, 3H,
pyrimidine–CH3); 13C NMR (DMSO-d6, ppm) δ: 170.79,
169.79, 166.56, 156.27 (q, J = 34.5 Hz), 148.09, 145.31,
141.51, 137.17, 134.37, 131.14, 122.47, 122.13, 121.54,
103.42, 93.15, 26.02; IR (KBr, cm−1): ν 1658.9, 1526.7,
1506.5, 1453.4, 1392.7, 1317.4, 1189.2, 1142.9, 1087.9,
898.9; MS (ESI) m/z: 577.5 ([M+H]+); Anal. calcd. for
C19H12BrF3IN3O2: C 39.47, H 2.09, N 7.27; found C 39.45,
H 2.10, N 7.25.
1
78.0%; m.p. 165–167 °C; H NMR (DMSO-d6, ppm) δ:
10.68 (s, 1H, –CONH–), 8.77 (m, 1H, Ph-H), 8.43 (m,
1H, Ph-H), 7.87 (d, 2H, J = 9.15 Hz, Ph-H), 7.80 (m, 1H,
Ph-H), 7.49 (s, 1H, pyrimidine-H), 7.29 (d, 2H, J=9.15 Hz,
Ph-H), 2.52 (s, 3H, pyrimidine–CH3); 13C NMR (DMSO-
d6, ppm) δ: 170.78, 169.78, 166.51(d, J=275.40 Hz)163.00,
156.29(q, J = 34.6 Hz), 155.89, 153.74, 148.27, 137.19,
136.99, 136.29, 136.21, 132.07, 126.33, 122.44, 122.38,
122.09, 119.52, 119.35, 103.38, 25.99; 13C NMR (DMSO-
d6, 125 MHz) δ: 170.79, 169.78, 163.45, 163.26, 161.46,
148.23, 139.02, 138.96, 136.99, 127.32, 122.69, 122.49,
122.35, 114.83, 114.64, 103.38, 26.00; IR (KBr, cm−1): ν
3446.9, 3339.8, 1653.0, 1610.6, 1576.8, 1545.0, 1510.3,
1411.9, 1395.5, 1193.9, 1150.6, 902.7, 814.0, 511.1; Anal.
calcd. for C19H12F4N4O4: C 52.30, H 2.77, N 12.84; found
C 52.34, H 2.75, N 12.85.
4‑Bromo‑N‑(4‑((2‑methyl‑6‑(trifuoromethyl)pyrimidin‑4‑yl)
oxy)phenyl)‑2‑nitrobenzamide (4y) Yellow solid; yield
1
85.3%; m.p. 216–218 °C; H NMR (DMSO-d6, ppm) δ:
10.85 (s, 1H, –CONH–), 8.39 (s, 1H, Ph-H), 8.14 (d, 1H,
J=10.3 Hz, Ph-H), 7.78 (m, 3H, Ph-H), 7.51 (s, 1H, pyrim-
idine-H), 7.28 (d, 2H, J=9.2 Hz, Ph-H), 2.52 (s, 3H, pyrimi-
dine–CH3); 13C NMR (DMSO-d6, ppm) δ: 170.77, 169.79,
163.70, 156.30 (q, J = 23.6 Hz), 148.20, 147.91, 137.24,
136.98, 131.81, 131.56, 127.54, 123.78, 122.58, 121.56,
103.46, 26.00; IR (KBr, cm−1): ν 1660.8, 1543.1, 1509.4,
1388.8, 1351.2, 1267.3, 1195.9, 1152.5, 1091.7, 984.7,
872.8; MS (ESI) m/z: 497.5 ([M+H]+); Anal. calcd. for
C19H12F3N4O4: C 45.90, H 2.43, N 11.27; found: C 45.93,
H 2.40, N 11.25.
3‑Bromo‑N‑(4‑((2‑methyl‑6‑(trifuoromethyl)pyrimidin‑4‑yl)
oxy)phenyl)‑5‑(trifuoromethyl)benzamide (4v) White solid;
yield 88.6%; m.p. 192–194 °C; 1H NMR (DMSO-d6, ppm)
δ: 10.66 (s, 1H, –CONH–), 8.47 (s, 1H, Ph-H), 8.29 (s, 1H,
Ph-H), 8.25 (s, 1H, Ph-H), 7.86 (d, 2H, J=9.2 Hz, Ph-H),
7.50(s, 1H, pyrimidine-H), 7.30 (d, 2H, J=9.2 Hz, Ph-H),
2.53 (s, 3H, pyrimidine–CH3); 13C NMR (DMSO-d6, ppm)
δ: 170.78, 169.78, 163.15, 156.28 (q, J=34.6 Hz), 148.32,
138.21, 136.93, 135.07, 131.52(q, J = 31.6 Hz), 131.46,
124.13, 123.44, 122.44, 122.40, 103.40, 26.00; IR (KBr,
cm−1): ν 3283.0, 1649.2, 1578.8, 1543.1, 1507.4, 1394.6,
1386.9, 1336.7, 1312.6, 1192.1, 1144.8, 1045.5, 986.6,
898.9; MS (ESI) m/z: 520.3 ([M+H]+); Anal. calcd. for
C19H13BrF3N3O2: C 50.46, H 2.90, N 9.29; found: C 50.47,
H 2.87, N 9.26
4‑Chloro‑N‑(4‑((2‑methyl‑6‑(trifuoromethyl)pyrimidin‑4‑yl)
oxy)phenyl)‑3‑nitrobenzamide (4z) White crystals; yield
1
82.1%; m.p. 197–199 °C; H NMR (DMSO-d6, ppm) δ:
10.66 (s, 1H, –CONH–), 8.63 (s, 1H, Ph-H), 8.26 (dd, 1H, J1
= 2.3 Hz, J2 = 8.6 Hz, Ph-H), 7.84 (d, 2H, J=8.6 Hz, Ph-H),
7.48 (s, 1H, pyrimidine-H), 7.28 (d, 2H, J=8.6 Hz, Ph-H),
2.52 (s, 3H, pyrimidine–CH3); 13C NMR (DMSO-d6, ppm)
δ: 170.77, 169.78, 163.05, 156.30 (q, J =34.6 Hz), 148.31,
147.91, 136.93, 135.32, 133.38, 132.54, 128.70, 125.42,
122.39, 103.40, 26.00; IR (KBr, cm−1): ν 1654.0, 1533.5,
1397.5, 1330.0, 1190.1, 1144.8, 1118.8, 1048.4, 985.7,
898.9; MS (ESI) m/z: 453.2 ([M+H]+), 475.4([M+Na]+);
Anal. calcd. for C19H12BrF3N4O4: C 50.40, H 2.67, N 12.37;
found: C 50.42, H 2.68, N 12.34.
4‑Bromo‑2‑iodo‑N‑(4‑((2‑methyl‑6‑(trifuoromethyl)pyrimi‑
din‑4‑yl)oxy)phenyl)benzamide (4w) Yellow solid; yield
1
80.7%; m.p. 175–177 °C; H NMR (DMSO-d6, ppm) δ:
10.66 (s, 1H, –CONH–), 7.88 (d, 1H, J = 6.3 Hz, Ph-H),
7.80 (d, 3H, J = 8.6 Hz, Ph-H), 7.50 (s, 1H, pyrimidine-
H), 7.39(t, 1H, J=9.15 Hz, Ph-H), 7.28(d, 2H, J=8.6 Hz,
Ph-H), 2.52 (s, 3H, pyrimidine–CH3); 13C NMR (DMSO-
d6, ppm) δ: 170.79, 169.78, 161.79, 156.29 (q, J=36.5 Hz),
148.14, 137.01, 135.63, 132.69, 127.57, 122.49, 121.65,
119.34, 119.15, 116.72, 103.38, 26.00; IR (KBr, cm−1): ν
3339.8, 1653.1, 1576.9, 1545.1, 1510.3, 1475.6, 1395.6,
1386.9, 1186.3, 1098.5, 985.7, 868.0; MS (ESI) m/z: 577.3
([M+H]+); Anal. calcd. for C19H12BrF3IN3O2: C 39.47, H
2.09, N 7.27; found: C 39.48, H 2.08, N 7.27.
N‑(4‑((2‑methyl‑6‑(trifluoromethyl)pyrimidin‑4‑yl)oxy)
phenyl)‑3,5‑bis(trifluoromethyl)benzamide (4aa) White
solid; yield 80.1%; m.p. 191–193 °C; 1H NMR (DMSO-d6,
ppm) δ: 10.78 (s, 1H, –CONH–), 8.62 (s, 2H, Ph-H), 8.39
(s, 2H, Ph-H), 7.86 (d, 2H, J=8.6 Hz, Ph-H), 7.49 (s, 1H,
pyrimidine-H), 7.31 (d, 1H, J=8.6 Hz, Ph-H), 2.53 (s, 3H,
pyrimidine–CH3); 13C NMR (DMSO-d6, ppm) δ: 176.96,
170.81, 169.79, 163.14, 156.30 (q, J = 34.6 Hz), 148.24,
130.85, 129.09, 122.65(q, J = 34.6 Hz), 122.38, 103.40,
26.00; IR (KBr, cm−1): ν 1655.7, 1545.1, 1507.4, 1452.5,
5‑Bromo‑2‑iodo‑N‑(4‑((2‑methyl‑6‑(trifuoromethyl)pyrimi‑
din‑4‑yl)oxy)phenyl)benzamide (4x) Yellow crystals; yield
1
81.3%; m.p. 258–260 °C; H NMR (DMSO-d6, ppm) δ:
1 3