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(t, J = 8.8 Hz, 2H, Ar–H), 6.96 (t, J = 7.6 Hz, 1H, Ar–H), 6.92 (d, J = 4.4
Hz, 2H, Ar–H), 6.35 (s, 1H, Ar–H), 4.93 (s, 2H, OCH2), 2.25 (s, 3H,
CH3); 13C NMR (400 MHz, DMSO d6): d167.30, 165.20, 160.99,
156.84, 151.36, 139.85, 129.15, 122.12, 119.84, 116.21, 100.34,
67.64, 23.37; LCMS: m/z calculated for C19H17FN4O2: 352.4; found:
353.4 [M+1]+.
4.1.5.10. 2-(4-Chlorophenoxy)-N-(4-methyl-6-(p-tolylamino) pyrim-
idin-2-yl) acetamide (6j). White solid; yield: 41.65%; M.P.: 191–
194 °C; IR (KBr)
m
(cmÀ1): 3242, 3186, 2989, 1681, 1058; 1H NMR
(400 MHz, DMSO d6): d10.29 (s, 1H, CONH), 9.38 (s, 1H, NH), 7.65
(d, J = 8 Hz, 2H, Ar–H), 7.32 (d, J = 8.8 Hz, 2H, Ar–H), 7.09 (d, J = 8.
4 Hz, 2H, Ar–H), 6.92 (d, J = 8.8 Hz, 2H, Ar–H), 6.29 (s, 1H, Ar–H),
4.96 (s, 2H, OCH2), 2.23 (s, 6H, CH3); 13C NMR (400 MHz, DMSO d6):
d167.43, 165.05, 161.06, 156.85, 156.48, 137.18, 131.18, 129.12,
129.10, 124.46, 120.19, 116.21, 99.99, 67.72, 23.35, 20.37; LC-
MS: m/z calculated for C20H19ClN4O2: 382.8; found: 383.4 [M+1]+,
385.4 [M+2]+.
4.1.5.5. N-(4-methyl-6-(p-tolylamino)pyrimidin-2-yl)-2-phenoxyac-
etamide (6e). White solid; yield: 46.26%; M.P.: 205–206 °C; IR
(KBr)
m
(cmÀ1): 3363, 3301, 3035, 1681, 1066; 1H NMR (400
MHz, DMSO d6): d10.27 (s, 1H, CONH), 9.40 (s, 1H, NH), 7.67 (d, J
= 8.0 Hz, 2H, Ar–H), 7.28 (t, J = 8.0 Hz, 2H, Ar–H), 7.07 (d, J = 8.0 H
z, 2H, Ar–H), 6.94 (t, J = 7.2 Hz, 1H, Ar–H), 6.89 (d, J = 8.0 Hz, 2H,
Ar–H), 6.29 (s, 1H, Ar–H), 4.93 (s, 2H, OCH2), 2.23 (s, 6H, CH3);
13C NMR (400 MHz, DMSO d6): d167.54, 165.05, 161.05, 157.92,
156.49, 137.23, 131.11, 129.41, 129.10, 120.80, 120.10, 114.41,
100.01, 67.37, 23.35, 20.38; LC-MS: m/z calculated for
4.1.5.11. 2-(4-fluorophenoxy)-N-(4-((4-methoxyphenyl) amino) -6-
Methylpyrimidin- 2-yl) acetamide (6k). White solid; yield: 55.25%;
M.P.: 192–194 °C; IR (KBr)
m
(cmÀ1): 3236, 3155, 2977, 1681,
1062; 1H NMR (400 MHz, DMSO d6): d10.25 (s, 1H, CONH), 9.33
(s, 1H, NH), 7.67 (d, J = 8 Hz, 2H, Ar–H), 7.13 (d, J = 8.8 Hz, 2H,
Ar–H), 6.90 (d, J = 4.4 Hz, 4H, Ar–H), 6.24 (s, 1H, Ar–H), 4.91 (s,
2H, OCH2), 3.70 (s, 3H, OCH3), 2.22 (s, 3H, CH3); 13C NMR (400
MHz, DMSO d6): d167.57, 164.94, 161.13, 157.76, 156.61, 155.41,
154.83, 154.28, 132.74, 121.95, 115.84, 115.66, 113.87, 99.60,
68.01, 55.07, 23.33; LC-MS: m/z calculated for C20H19FN4O3:
382.4; found: 383.3 [M+1]+.
C
20H20N4O2: 348.4; found: 349.4 [M+1]+.
4.1.5.6. N-(4-((4-methoxyphenyl)amino)-6-methylpyrimidin-2-yl)-2-
phenoxyacetamide (6f). White solid; yield: 56.22%; M.P.: 175–177
°C; IR (KBr)
m
(cmÀ1): 3242, 3218, 2937, 1679, 1062; 1H NMR (400
MHz, DMSO d6): d10.28 (s, 1H, CONH), 9.35 (s, 1H, NH), 7.69 (d, J =
8.0 Hz, 2H, Ar–H), 7.26 (t, J = 7.6 Hz, 2H, Ar–H), 6.945 (t, J = 7.6 Hz
1H, Ar–H), 6.88 (d, J = 8.8 Hz, 4H, Ar–H), 6.24 (s, 1H, Ar–H), 4.92 (s,
2H, OCH2), 3.70 (s, 3H, OCH3), 2.22 (s, 3H, CH3); 13C NMR (400 MHz,
DMSO d6): d167.59, 164.91, 161.09, 157.88, 156.49, 154.77, 132.75,
129.39, 121.82, 120.77, 114.36, 113.84, 100.09, 67.34, 55.05, 23.32;
LC-MS: m/z calculated for C20H20N4O3: 364.4; found: 365.2 [M+1]+.
4.1.5.12.
amino)-6-methylpyrimidin-2-yl)acetamide (6l). White solid; yield:
48.29%; M.P.: 189–190 °C; IR (KBr)
(cmÀ1): 3240, 3122, 2962,
2-(3-Chloro-4-methylphenoxy)-N-(4-((4-methoxyphenyl)
m
1683, 1037; 1H NMR (400 MHz, DMSO d6): d10.25 (s, 1H, CONH),
9.34 (s, 1H, NH), 7.66 (d, J = 7.2 Hz, 2H, Ar–H), 7.29 (s, 1H, Ar–H),
6.91 (d, J = 2.8 Hz, 1H, Ar–H), 6.86 (d, J = 8.8 Hz, 2H, Ar–H), 6.73
(d, J = 2.8 Hz, 1H, Ar–H), 6.24 (s, 1H, Ar–H), 4.93 (s, 2H, OCH2),
3.69 (s, 3H, OCH3), 2.27 (s, 3H, CH3), 2.22 (s, 3H, CH3); 13C NMR
(400 MHz, DMSO d6): d167.52, 164.94, 161.11, 156.74, 156.51,
154.80, 136.34, 132.73, 129.37, 124.77, 121.91, 117.28, 113.45,
4.1.5.7. N-(4-methyl-6-(p-tolylamino)pyrimidin-2-yl)-2-(o-tolyloxy)
acetamide (6g). White solid; yield: 39.56%; M.P.: 196–199 °C; IR
(KBr)
m
(cmÀ1): 3242, 2937, 1679, 1600, 1492, 1280, 1247, 1031,
823; 1H NMR (400 MHz, DMSO d6): d10.24 (s, 1H, CONH), 9.41 (s,
1H, NH), 7.68 (d, J = 8.0 Hz, 2H, Ar–H), 7.12 (t, J = 7.2 Hz, 1H, Ar–
H), 7.09 (d, J = 8.0 Hz, 2H, Ar–H), 6.84 (t, J = 7.6 Hz, 1H, Ar–H),
6.75 (d, J = 8.4 Hz 1H, Ar–H), 6.30 (s, 1H, Ar–H), 4.96 (s, 2H,
OCH2), 2.50 (s, 6H, CH3), 1.99 (s, 3H, CH3); 13C NMR (400 MHz,
DMSO d6): d167.54, 165.05, 161.05, 157.92, 156.49, 137.23,
131.11, 129.41, 126.60, 120.10, 114.41, 100.01, 67.37, 23.35,
20.38, 20.02; LC-MS: m/z calculated for C21H22N4O2: 362.4; found:
363.5 [M+1]+.
100, 67.63, 55.06, 23.34, 19.76; LC-MS: m/z calculated for C21H21
-
ClN4O3: 412.9; found: 413.2 [M+1]+, 415.3 [M+2]+.
4.1.5.13. N-(4-((4-fluorophenyl)amino)-6-methylpyrimidin-2-yl)-2-
phenoxyacetamide (6m). White solid; yield: 40.95%; M.P.: 178–
180 °C; IR (KBr)
m
(cmÀ1): 3249, 3128, 2993, 1681, 1066; 1H NMR
(400 MHz, DMSO d6): d10.36 (s, 1H, CONH), 9.55 (s, 1H, NH), 7.89
(d, J = 4.8 Hz, 2H, Ar–H), 7.87 (d, J = 7.2 Hz, 2H, Ar–H), 7.29 (t, J =
6.8 Hz, 2H, Ar–H), 7.12 (t, J = 7.2 Hz, 1H, Ar–H), 6.97 (d, J = 8.0 Hz,
2H, Ar–H), 6.30 (s, 1H, Ar–H), 4.98 (s, 2H, OCH2), d 2.25 (s, 3H,
CH3); 13C NMR (400 MHz, DMSO d6): d167.53, 165.20, 160.85,
158.64, 156.38, 156.27, 138.31, 129.54, 121.40, 117.97, 114.97,
100.22, 67.45, 23.31; LC-MS: m/z calculated for C19H17FN4O2:
352.4; found: 353.5 [M+1]+.
4.1.5.8. N-(4-((4-methoxyphenyl)amino)-6-methylpyrimidin-2-yl)-2-
(m-tolyloxy)acetamide (6h). White solid; yield: 44.43%; M.P.: 162–
164 °C; IR (KBr)
m
(cmÀ1): 3245, 3093, 2958, 1681, 1074; 1H NMR
(400 MHz, DMSO d6): d10.24 (s, 1H, CONH), 9.35 (s, 1H, NH), 7.69
(d, J = 6.4 Hz, 2H, Ar–H), 7.16 (t, J = 7.6 Hz 1H, Ar–H), 6.86 (d, J = 8
.4 Hz, 2H, Ar–H), 6.76 (d, J = 7.2 Hz, 1H, Ar–H), 6.67 (d, J = 8.Hz,
1H, Ar–H), 6.24 (s, 2H, Ar–H), 4.90 (s, 2H, OCH2), 3.70 (s, 3H,
OCH3), 2.26 (s, 6H, CH3); 13C NMR (400 MHz, DMSO d6): d167.63,
164.91, 161.09, 157.92, 156.51, 154.74, 138.87, 132.80, 129.14,
121.79, 121.57, 115.10, 113.85, 111.31, 99.69, 67.31, 55.06, 23.33,
4.1.5.14. N-(4-((2-fluorophenyl)amino)-6-methylpyrimidin-2-yl)-2-
phenoxyacetamide (6n). White solid; yield: 34.76%; M.P.: 183–
186 °C; IR (KBr)
m
(cmÀ1): 3234, 3126, 2991, 1677, 1070; 1H NMR
(400 MHz, DMSO-d6): d10.29 (s, 1H, CONH), 9.24 (s, 1H, NH),
8.31 (d, J = 8.0 Hz, 1H, Ar–H), 7.29 (t, J = 7.6 Hz, 1H, Ar–H), 7.15
(d, J = 6.4 Hz, 2H, Ar–H), 7.11 (t, J = 3.6 Hz, 1H, Ar–H), 7.09 (d, J =
2.0 Hz, 1H, Ar–H), 6.95 (t, J = 7.2 Hz, 1H, Ar–H), 6.86 (d, J = 8.4 Hz,
2H, Ar–H), 6.47 (s, 1H, Ar–H), 4.89 (s, 2H, OCH2), 2.25 (s, 3H,
CH3); 13C NMR (400 MHz, DMSO d6): d167.84, 165.72, 161.38,
157.90, 156.39, 155.02, 138.83, 129.11, 127.01, 124.44, 121.53,
115.31, 114.31, 100.32, 67.24, 23.40; LC-MS: m/z calculated for
21.07; LC-MS: m/z calculated for
C21H22N4O3: 378.4; found:
379.3 [M+1]+.
4.1.5.9. N-(4-Methyl-6-(p-tolylamino)pyrimidin-2-yl)-2-(p-tolyloxy)
acetamide (6i). Orange solid; yield: 44.07%; M.P.: 205–206 °C; IR
(KBr)
m
(cmÀ1): 3330, 3220, 2943, 1687, 1070; 1H NMR (400
MHz, DMSO d6): d10.20 (s, 1H, CONH), 9.39 (s, 1H, NH), 7.68 (d, J
= 7.6 Hz, 2H, Ar–H), 7.082 (d, J = 4.0 Hz, 4H, Ar–H), 6.79 (d, J = 8.0
Hz, 2H, Ar–H), 6.30 (s, 1H, Ar–H), 4.88 (s, 2H, OCH2), 2.22 (s, 9H,
CH3); 13C NMR (400 MHz, DMSO d6): d167.64, 165.03, 161.07,
156.50, 155.83, 137.25, 131.09, 129.72, 129.48, 129.09, 120.10,
114.25, 100.07, 67.55, 23.33, 20.37, 20.02; LC-MS: m/z calculated
for C21H22N4O2: 362.4; found: 363.5 [M+1]+.
C
19H17FN4O2: 352.4; found: 353.5 [M+1]+.
4.1.5.15. N-(4-((3-chlorophenyl)amino)-6-methylpyrimidin-2-yl)-2-
phenoxyacetamide (6o). White solid; yield: 45.29%; M.P.: 172–
174 °C; IR (KBr)
(400 MHz, DMSO-d6): d10.44 (s, 1H, CONH), 9.70 (s, 1H, NH),
m
(cmÀ1): 3251, 3136, 2935, 1683, 1078; 1H NMR