Med Chem Res
C–H), 7.95 (s, 1H, N–H), 7.79–7.81 (m, 2H, Ar–H),
1H, N–H), 7.38–7.51 (m, 4H, Ar–H), 7.26–7.30 (m, 1H,
Ar–H), 6.97–7.07 (m, 1H, Ar–H), 6.95–6.97 (d, 1H J =
8.2 Hz, Ar–H), 6.45 (s, 1H, C(5)–H-pyrimidine), 3.73 (s,
7
7
.64–7.66 (m, 2H, Ar–H), 7.41–7.49 (m, 5H, Ar–H),
.29–7.33 (t, 1H J = 7.4 Hz, Ar–H), 6.51 (s, 1H, C(5)–H-
1
3
13
pyrimidine), 2.39 (s, 6H, CH3); C NMR (d ppm, CDCl3,
00 MHz): 168.29 (C-4, C-6-pyrimidine), 159.37 (C-2-
pyrimidine), 152.43 (C-3-pyrazole), 139.63 (C=N), 135.47
Ar), 132.44 (Ar), 129.50 (C-5-pyrazole), 128.72 (Ar),
28.58 (Ar), 128.49 (Ar), 126.86 (Ar), 126.41 (Ar), 119.13
3H, OCH ), 2.35 (s, 6H, CH ). C NMR (d ppm, CDCl3,
3
3
1
100 MHz): 168.20 (C-4, C-6-pyrimidine), 159.54 (C-2-
pyrimidine), 156.88 (Ar), 150.20 (C-3-pyrazole), 139.73
(C=N), 136.95 (Ar), 131.68 (Ar), 130.27 (Ar), 129.40 (C-5-
pyrazole), 126.61 (Ar), 125.38 (Ar), 121.43 (Ar) 120.99
(Ar), 119.04 (Ar), 118.38 (Ar), 112.27 (C-5-pyrimidine),
111.17 (C-4-pyrazole), 55.52 (OCH ), 23.93 (CH ); Anal.
(
1
(
(
Ar), 116.83 (C-5-pyrimidine), 112.58 (C-4-pyrazole), 23.9
CH ); Anal. Calculated for C H N (C, H, N): C 71.72,
3
22 20
6
3
3
H 5.47, N 22.81; Found: C 71.57, H 5.47, N 22.60.
Calculated for C H N O (C, H, N, O): C 69.33, H 5.57, N
23 22 6
21.09, O 4.02; Found: C 69.86, H 5.84, N 21.25, O 3.04.
2
-((1-Phenyl-3-p-tolyl-1H-pyrazol-4-yl)methylene)-1-(4,6-
-
1
dimethylpyrimidin-2-yl)-hydrazine (3b) IR (mmax cm
KBr): 3,183 cm (–NH str.); H NMR (d ppm, CDCl ,
,
2-((3-(4-Nitrophenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)-1-
-1
(4,6-dimethylpyrimidin-2-yl) hydrazine (3e) IR (mmax cm ,
-
1
1
3
-
1
1
4
00 MHz): 8.75 (s, 1H, C(5)H-pyrazole), 8.66 (s, 1H, N=
C–H), 7.95 (s, 1H, N–H), 7.78–7.82 (m, 2H, Ar–H),
.52–7.54 (d, 2H, J = 8.0 Hz, Ar–H), 7.44–7.48 (m, 2H,
Ar–H), 7.25–7.32 (m, 3H, Ar–H), 6.50 (s, 1H, C(5)–H-
KBr): 3,140 cm (–NH str.); H NMR (d ppm, DMSO,
400 MHz): 11.12 (s, 1H, N–H), 8.83 (s, 1H, C(5)H-pyra-
zole), 8.34 (s, 1H, N=C–H), 8.31 (s, 4H, Ar–H), 7.93–7.95
(d, 2H, J = 8.2 Hz, Ar–H), 7.50–7.54 (t, 2H, J = 7.6 Hz,
Ar–H), 7.34–7.38 (t, 1H, J = 7.4, Ar–H), 6.56 (s, 1H,
7
1
3
pyrimidine), 2.41 (s, 3H, CH ). 2.39 (s, 6H, CH );
3
C
3
1
3
NMR (d ppm, CDCl , 100 MHz): 168.30 (C-4, C-6-
pyrimidine), 159.52 (C-2-pyrimidine), 152.51 (C-3-pyra-
C(5)–H-pyrimidine), 2.36 (s, 6H, CH3); C NMR (d ppm,
DMSO, 100 MHz): 167.13 (C-4, C-6-pyrimidine), 159.27
(C-2-pyrimidine), 153.19 (C-3-pyrazole), 148.10 (Ar),
146.79 (Ar), 138.97 (C=N), 138.85 (Ar), 133.85 (Ar),
129.30 (C-5-pyrazole), 129.21 (Ar), 128.13 (Ar), 126.80
(Ar), 123.21 (Ar), 118.53 (C-5-pyrimidine), 111.35 (C-4-
pyrazole), 23.44 (CH ); Anal. Calculated for C H N O
22 19 7 2
3
zole), 139.70 (C=N), 138.38 (Ar), 135.56 (Ar), 129.58 (C-
5
-pyrazole), 129.49 (Ar), 129.42 (Ar), 128.47 (Ar), 126.78
Ar), 126.29 (Ar), 119.12 (Ar), 116.76 (C-5-pyrimidine),
12.56 (C-4-pyrazole), 24.01 (CH ), 21.35 (CH ); Anal.
(
1
3
3
Calculated for C H N (C, H, N): C 72.23, H 5.80,
6
2
3
22
3
N 21.97; Found: C 72.16, H 5.87, N 21.97.
(C, H, N, O): C 63.91, H 4.63, N 23.72, O 7.74; Found: C
3.82, H 4.90, N 23.58, O 7.71.
6
2
-((3-(4-Methoxyphenyl)-1-phenyl-1H-pyrazol-4-yl)methy-
lene)-1-(4,6-dimethylpyrimidin-2-yl) hydrazine (3c) IR
-
2-((3-(3-Nitrophenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)-1-
-1
1
-1
1
(
mmax cm , KBr): 3,225 cm (–NH str.); H NMR (d
(4,6-dimethylpyrimidin-2-yl) hydrazine (3f) IR (mmax cm ,
-
1
1
ppm, DMSO, 400 MHz): 11.81 (s, 1H, N–H), 9.01 (s, 1H,
C(5)H-pyrazole), 8.35 (s, 1H, N=C–H), 7.92–7.94 (d, 2H,
J = 7.76 Hz, Ar–H) 7.68–7.71 (d, 2H, J = 8.7 Hz, Ar–H),
KBr): 3,070 cm (–NH str.); H NMR (d ppm, DMSO,
400 MHz): 11.04 (s, 1H, N–H), 8.92 (s, 1H, C(5)H-pyra-
zole), 8.69–8.70 (t, 1H, J = 1.92 Hz, Ar–H), 8.50–
8.53 (m, 1H, Ar–H), 8.31 (s, 1H, N=C–H), 8.26–8.29 (m,
1H, Ar–H), 7.98–8.00 (m, 2H, Ar–H), 7.77–7.81 (t, 1H,
J = 8.0 Hz, Ar–H), 7.52–7.56 (t, 2H, J = 7.8 Hz, Ar–H),
7.35–7.39 (t, 1H, J = 7.4 Hz, Ar–H), 6.56 (s, 1H, C(5)–H-
7
.50–7.54 (m, 2H, Ar–H), 7.25–7.32 (t, 1H, J = 7.4 Hz,
Ar–H), 7.03–7.06 (d, 2H, J = 8.7 Hz, Ar–H), 6.72 (s, 1H,
C(5)–H-pyrimidine), 3.85 (s, 3H, OCH ), 2.43 (s, 6H,
3
1
3
CH3); C NMR (d ppm, CDCl , 100 MHz): 168.31 (C-4,
3
1
3
C-6-pyrimidine), 159.94 (Ar), 159.49 (C-2-pyrimidine),
pyrimidine), 2.30 (s, 6H, CH3); C NMR (d ppm, DMSO,
100 MHz): 167.13 (C-4, C-6-pyrimidine) 159.63 (C-2-
pyrimidine), 148.09 (C-3-pyrazole), 147.84 (Ar), 138.91
(C=N), 134.88 (Ar), 134.22 (Ar), 133.38 (Ar), 129.78 (Ar),
129.45 (C-5-pyrazole), 128.36 (Ar), 126.85 (Ar), 122.73
(Ar), 118.58 (Ar), 118.12 (Ar), 113.05 (C-5-pyrimidine),
1
52.29 (C-3-pyrazole), 139.70 (C=N), 135.52 (Ar), 129.85
C-5-pyrazole), 129.49 (Ar), 126.75 (Ar), 126.32 (Ar),
25.00 (Ar), 119.09 (Ar), 116.61 (Ar), 114.19 (C-5-
pyrimidine), 112.59 (C-4-pyrazole), 55.40 (OCH ), 24.01
(
1
3
(
CH ); Anal. Calculated for C H N O (C, H, N, O): C
3 23 22 6
6
2
9.33, H 5.57, N 21.09, O 4.02; Found: C 69.18, H 5.98, N
0.92, O 3.92.
111.31 (C-4-pyrazole), 23.45 (CH ); Anal. Calculated for
3
C H N O (C, H, N, O): C 63.91, H 4.63, N 23.72, O
22 19 7 2
7.74; Found: C 63.14, H 4.63, N 23.46, O 8.77.
2
-((3-(2-Methoxyphenyl)-1-phenyl-1H-pyrazol-4-yl)methy-
lene)-1-(4,6-dimethylpyrimidin-2-yl) hydrazine (3d) IR
1
2-((3-(4-Chlorophenyl)-1-phenyl-1H-pyrazol-4-yl)methy-
-
1
-1
(
mmax cm , KBr): 3,172 cm (–NH str.); H NMR (d
ppm, CDCl , 400 MHz): 8.83 (s, 1H, C(5)H-pyrazole),
lene)-1-(4,6-dimethylpyrimidin-2-yl) hydrazine (3g) IR
-
1
-1
1
(mmax cm , KBr): 3,217 cm (–NH str.); H NMR (d
ppm, CDCl , 400 MHz): 8.65 (s, 1H, C(5)H-pyrazole),
3
8
.65 (s, 1H, N=C–H), 7.77–7.79 (m, 2H, Ar–H), 7.66 (s,
3
123