892
L. Rong, H. Han, H. Jiang, Y. Dai, M. Zhuang, M. Cao, and S. Tu
Vol 46
1
1012, 841, 777, 756, 720, 690, 648 cmꢁ1; H NMR: (400 Hz,
DMSO-d6), (d, ppm): 2.75 (3H, s, CH3), 7.40 (2H, d, J ¼ 8.8
Hz, J ¼ 8.8 Hz, ArH), 7.57 (3H, t, J ¼3.6 Hz, J ¼ 2.8 Hz,
ArH), 8.33–8.36 (2H, m, ArH), 8.41–8.45 (3H, m, ArH). Anal.
Calcd for C17H13FN2: C, 77.25; H, 4.96; N, 10.60. Found: C,
77.40; H, 4.94; N, 10.56. HRMS m/z calculated for C17H13FN2
[M þ H]: 265.1141; found: 265.1146.
74.62; H, 5.89; N, 9.18. HRMS m/z calculated for C19H18N2O2
[M þ H]: 307.1447; found: 307.1446.
4-(3-Chlorophenyl)-6-(4-methoxyphenyl)-2-methylpyrimi-
dine (4h). This compound was obtained as white crystals, mp
85–86ꢀC; IR: (KBr, m, cmꢁ1): 3066, 2974, 2938, 2842, 1608,
1572, 1511, 1462, 1420, 1364, 1292, 1240, 1192, 1174, 1027,
831, 802, 691, 590 cmꢁ1 1H NMR: (400 Hz, DMSO-d6), (d,
;
2-Methyl-4-phenyl-6-p-tolylpyrimidine (4c). This compound
was obtained as white crystals, mp 99–100ꢀC; IR: (KBr, m,
cmꢁ1): 3034, 2920, 1572, 1528, 1448, 1390, 1367, 1344, 1305,
1235, 1186, 1122, 1077, 1021, 989, 904, 875, 834, 818, 782,
ppm): 2.71 (3H, s, CH3), 3.86 (3H, s, OCH3), 7.10 (2H, d, J ¼
8.8 Hz, ArH), 7.57–7.63 (2H, m, ArH), 8.30 (1H, d, J ¼ 7.2
Hz, ArH), 8.34 (2H, d, J ¼ 8.8 Hz, ArH), 8.39 (2H, s, ArH).
Anal. Calcd for C18H15ClN2O: C, 69.57; H, 4.86; N, 9.01.
Found: C, 69.66; H, 4.84; N, 9.05. HRMS m/z calculated for
C18H15ClN2O [M þ H]: 311.0951; found: 311.0951.
759, 717, 698, 648 cmꢁ1 1H NMR: (400 Hz, DMSO-d6), (d,
;
ppm): 2.40 (3H, s, CH3), 2.74 (3H, s, CH3), 7.37 (2H, d, J ¼ 8.0
Hz, ArH), 7.56 (3H, t, J ¼ 3.6 Hz, J ¼ 3.6 Hz, ArH), 8.25 (2H,
d, J ¼ 8.0 Hz, ArH), 8.32–8.34 (2H, m, ArH), 8.36 (1H, s, ArH).
Anal. Calcd for C18H16N2: C, 83.04; H, 6.19; N, 10.76. Found:
C, 83.20; H, 6.17; N, 10.72. HRMS m/z calculated for C18H16N2
[M þ H]: 261.1392; found: 261.1390.
4-(3,4-Dimethylphenyl)-6-(4-methoxyphenyl)-2-methylpy-
rimidine (4i). This compound was obtained as white crystals,
mp 92–93ꢀC; IR: (KBr, m, cmꢁ1): 3010, 2966, 2938, 2919,
2841, 1610, 1574, 1455, 1410, 1360, 1339, 1303, 1243, 1171,
1
1113, 1025, 874, 828, 805, 761, 578 cmꢁ1; H NMR: (400 Hz,
DMSO-d6), (d, ppm): 2.30 (3H, s, CH3), 2.34 (3H, s, CH3), 2.71
(3H, s, CH3) 3.85 (3H, s, OCH3), 7.09 (2H, d, J ¼ 9.2 Hz,
ArH), 7.30 (1H, d, J ¼ 7.6 Hz, ArH), 8.05 (1H, d, J ¼ 8.0 Hz,
ArH), 8.20 (1H, s, ArH), 8.27 (1H, s, ArH), 8.31 (2H, d, J ¼ 8.8
Hz, ArH). Anal. Calcd for C20H20N2O: C, 78.92; H, 6.62; N,
9.20. Found: C, 78.78; H, 6.65; N, 9.16. HRMS m/z calculated
for C20H20N2O [M þ H]: 305.1654; found: 305.1654.
4-(4-Methoxyphenyl)-2-methyl-6-phenylpyrimidine (4d). This
compound was obtained as white crystals, mp 94–96ꢀC, Lit.
[13] 103–104ꢀC; IR: (KBr, m, cmꢁ1): 2965, 2842, 1602, 1573,
1441, 1368, 1295, 1255, 1185, 1170, 1030, 987, 874, 829,
783, 763, 727, 698, 589 cmꢁ1; H NMR: (400 Hz, DMSO-d6),
1
(d, ppm): 2.72 (3H, s, CH3), 3.85 (3H, s, OCH3), 7.10 (2H, d,
J ¼ 8.8 Hz, ArH), 7.56 (3H, t, J ¼ 2.8 Hz, J ¼ 3.2 Hz, ArH),
8.32 (5H, d, J ¼ 6.4 Hz, ArH). Anal. Calcd for C18H16N2O:
C, 78.24; H, 5.84; N, 10.14. Found: C, 78.19; H, 5.86; N,
10.18. HRMS m/z calculated for C18H16N2O [M þ H]:
277.1341; found: 277.1338.
4-(3,4-Dimethoxyphenyl)-6-(4-methoxyphenyl)-2-methyl-
pyrimidine (4j). This compound was obtained as white crys-
tals, mp 116–117ꢀC; IR: (KBr, m, cmꢁ1): 3086, 2997, 2960,
2931, 2833, 1574, 1510, 1439, 1362, 1345, 1293, 1251, 1172,
1117, 1095, 1020, 883, 832, 803, 765, 616, 575 cmꢁ1 1H
;
4-(4-Fluorophenyl)-6-(4-methoxyphenyl)-2-methylpyrimi-
dine (4e). This compound was obtained as white crystals, mp
107–109ꢀC; IR: (KBr, m, cmꢁ1): 3041, 3005, 2972, 2938,
2937, 1602, 1509, 1414, 1371, 1299, 1259, 1173, 1096, 1030,
NMR: (400 Hz, DMSO-d6), (d, ppm): 2.70 (3H, s, CH3), 3.85
(6H, s, 2 ꢂ OCH3), 3.90 (3H, s, CH3), 7.09–7.12 (3H, dd, J ¼
4.4 Hz, J ¼ 4.4 Hz, ArH), 7.86 (1H, d, J ¼ 2.0 Hz, ArH),
7.96 (1H, dd, J ¼ 2.0 Hz, J ¼ 2.0 Hz, ArH), 8.26 (1H, s,
ArH), 8.32 (2H, d, J ¼ 8.8 Hz, ArH). Anal. Calcd for
C20H20N2O3: C, 71.41; H, 5.99; N, 8.33. Found: C, 71.55; H,
5.97; N, 8.29. HRMS m/z calculated for C20H20N2O3 [M þ
H]: 337.1552; found: 337.1555.
846, 822, 764 cmꢁ1; H NMR: (400 Hz, DMSO-d6), (d, ppm):
1
2.71 (3H, s, CH3), 3.85 (3H, s, OCH3), 7.10 (2H, d, J ¼ 8.8
Hz, ArH), 7.39 (2H, t, J ¼ 8.8 Hz, J ¼ 8.8 Hz, ArH), 8.32
(3H, d, J ¼ 6.8 Hz, ArH), 8.38–8.42 (2H, dd, J ¼ 5.6 Hz, J ¼
5.6 Hz, ArH). Anal. Calcd for C18H15FN2O: C, 73.45; H, 5.14;
N, 9.52. Found: C, 73.51; H, 5.15; N, 9.50. HRMS m/z calcu-
lated for C18H15FN2O [M þ H]: 295.1247; found: 295.1248.
4-(4-Methoxyphenyl)-2-methyl-6-p-tolylpyrimidine (4f). This
compound was obtained as white crystals, mp 119–120ꢀC; IR:
(KBr, m, cmꢁ1): 3014, 2968, 2971, 2840, 1609, 1585, 1525,
1456, 1442, 1410, 1371, 1340, 1303, 1256, 1172, 1113, 1024,
4-(3-Chlorophenyl)-6-(4-fluorophenyl)-2-methylpyrimidine
(4k). This compound was obtained as white crystals, mp 105–
106ꢀC; IR: (KBr, m, cmꢁ1): 3020, 2925, 1582, 1537, 1505,
1365, 1296, 1221, 1158, 1126, 1096, 1013, 990, 869, 854, 832,
1
791, 764, 715, 688, 653 cmꢁ1; H NMR: (400 Hz, DMSO-d6),
(d, ppm): 2.71 (3H, s, CH3), 7.37 (2H, t, J ¼ 8.8 Hz, J ¼ 8.8
Hz, ArH), 7.58 (2H, t, J ¼ 8.8 Hz, J ¼ 8.8 Hz, ArH), 8.27 (1H,
d, J ¼ 7.2 Hz, ArH), 8.37–8.41 (4H, m, ArH). Anal. Calcd for
C17H12ClFN2: C, 68.35; H, 4.05; N, 9.38. Found: C, 68.45; H,
4.07; N, 9.34. HRMS m/z calculated for C17H12ClFN2 [M þ H]:
299.0751; found: 299.0751.
827, 776, 759, 574 cmꢁ1 1H NMR: (400 Hz, DMSO-d6), (d,
;
ppm): 2.40 (3H, s, CH3), 2.71 (3H, s, CH3), 3.86 (3H, s,
OCH3), 7.09 (2H, d, J ¼ 8.8 Hz, ArH), 7.36 (2H, d, J ¼ 8.0,
Hz, ArH), 8.23 (2H, d, J ¼ 8.0 Hz, ArH), 8.28 (1H, s, ArH),
8.32 (2H, d, J ¼ 8.4 Hz, ArH). Anal. Calcd for C19H18N2O:
C, 78.59; H, 6.25; N, 9.65. Found: C, 78.70; H, 6.27; N, 9.62.
HRMS m/z calculated for C19H18N2O [M þ H]: 291.1497;
found: 291.1499.
4,6-Bis(4-methoxyphenyl)-2-methylpyrimidine (4g). This
compound was obtained as white crystals, mp 159–160ꢀC; IR:
(KBr, m, cmꢁ1): 3006, 2969, 2939, 2839, 1606, 1525, 1455,
1416, 1374, 1302, 1255, 1171, 1113, 1026, 830, 777, 636, 575
4-(3-Chlorophenyl)-2-methyl-6-p-tolylpyrimidine (4l). This
compound was obtained as white crystals, mp 76–77ꢀC; IR:
(KBr, m, cmꢁ1): 3025, 2930, 1612, 1569, 1511, 1364, 1238,
1181, 1126, 1068, 989, 834, 815, 799, 761, 714, 690, 655, 646
cmꢁ1 1H NMR: (400 Hz, DMSO-d6), (d, ppm): 2.40 (3H, s,
;
CH3), 2.74 (3H, s, CH3), 7.37 (2H, d, J ¼ 8.0 Hz, ArH), 7.57–
7.64 (2H, m, ArH), 8.27 (2H, d, J ¼ 8.4 Hz, ArH), 8.31 (1H,
d, J ¼ 7.6 Hz, ArH), 8.41 (2H, d, J ¼ 9.2 Hz, ArH). Anal.
Calcd for C18H15ClN2: C, 73.34; H, 5.13; N, 9.50. Found: C,
73.45; H, 5.15; N, 9.47. HRMS m/z calculated for C18H15ClN2
[M þ H]: 295.1002; found: 295.1004.
cmꢁ1 1H NMR: (400 Hz, DMSO-d6), (d, ppm): 2.69 (3H, s,
;
CH3), 3.85 (6H, s, 2 ꢂ OCH3), 7.09 (4H, d, J ¼ 8.8 Hz,
ArH), 8.25 (1H, s, ArH), 8.32 (4H, d, J ¼ 8.8 Hz, ArH). Anal.
Calcd for C19H18N2O2: C, 74.49; H, 5.92; N, 9.14. Found: C,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet