Paper
28.1, 128.0, 113.8, 107.3, 58.6, 55.0, 16.3 ppm. FTIR (KBr, neat):
RSC Advances
1
5-(3-Chlorophenyl)-4-(4-chlorophenyl)-6-methyl-3,4-dihy-
ꢁ
1
n 3238, 1679, 1510, 1248, 1174, 834 cm . HRMS (ESI, m/z): [M + dropyrimidin-2(1H)-one (4e). 155.9 mg. Yield ¼ 94%. Yellow
+
ꢀ
1
H] , calcd for C H ClN O : 329.1051, found: 329.1054.
solid. Mp: 93.8–95.3 C. H NMR (400 MHz, DMSO-d ): d 8.59 (s,
1
8
18
2
2
6
5
-(4-Chlorophenyl)-6-methyl-4-(naphthalen-1-yl)-3,4-dihy-
1H), 7.45 (s, 1H), 7.32–7.29 (m, 2H), 7.22–7.15 (m, 4H), 7.11 (s,
1
3
dropyrimidin-2(1H)-one (3i). 112.3 mg. Yield ¼ 64%. Light 1H), 7.04–6.98 (m, 1H), 5.17 (s, 1H), 1.75 (s, 3H) ppm. C NMR
ꢀ
1
yellow solid. Mp: 250.4–251.6 C. H NMR (400 MHz, DMSO-d
6
6
): (100 MHz, DMSO-d ): d 153.1, 142.9, 140.2, 133.0, 132.1, 131.5,
d 8.58 (s, 1H), 8.29–8.19 (m, 1H), 7.92–7.86 (m, 1H), 7.82–7.75 130.1, 129.1, 128.9, 128.6, 128.3, 126.4, 107.0, 58.6, 16.4 ppm.
ꢁ
1
(
7
(
m, 1H), 7.53–7.40 (m, 4H), 7.36 (s, 1H), 7.15 (d, J ¼ 7.8 Hz, 2H), FTIR (KBr, neat): n 3236, 1682, 1489, 1239, 1091, 785 cm
.
1
3
+
.07 (d, J ¼ 8.0 Hz, 2H), 5.99 (s, 1H), 1.81 (s, 3H) ppm. C NMR HRMS (ESI, m/z): [M + H] , calcd for C H Cl N O: 333.0556,
1
7
15
2 2
100 MHz, DMSO-d ): d 152.7, 148.0, 144.0, 138.7, 136.9, 133.7, found: 333.0556.
6
1
1
1
31.1, 131.0, 130.6, 130.4, 128.6, 128.1, 127.9, 126.0, 125.9,
4-(4-Chlorophenyl)-5-(4-methoxyphenyl)-6-methyl-3,4-dihy-
25.6, 123.6, 106.8, 16.3 ppm. FTIR (KBr, neat): n 3230, 1703, dropyrimidin-2(1H)-one (4f). 140.5 mg. Yield ¼ 85%. Yellow
ꢁ1
+
ꢀ
1
493, 1253, 776 cm . HRMS (ESI, m/z): [M + H] , calcd for solid. Mp: 184.6–186.2 C. H NMR (400 MHz, DMSO-d ): d 8.42
6
C
21
H
5
18ClN
-(4-Chlorophenyl)-6-methyl-4-(thiophen-2-yl)-3,4-dihy-
dropyrimidin-2(1H)-one (3j). 128.8 mg. Yield ¼ 85%. Light NMR (100 MHz, DMSO-d ): d 157.6, 153.1, 143.3, 131.7, 130.5,
2
O: 349.1102, found: 349.1103.
(s, 1H), 7.35–7.29 (m, 3H), 7.19–7.14 (m, 2H), 6.99–6.94 (m, 2H),
6.82–6.76 (m, 2H), 5.07 (s, 1H), 3.68 (s, 3H), 1.71 (s, 3H) ppm. C
1
3
6
ꢀ
1
6
yellow solid. Mp: 193.2–194.4 C. H NMR (400 MHz, DMSO-d ): 129.8, 129.6, 128.7, 128.3, 113.6, 107.7, 58.9, 54.9, 16.2 ppm.
ꢁ1
d 8.63 (s, 1H), 7.55 (s, 1H), 7.35 (dd, J ¼ 5.0, 1.1 Hz, 1H), 7.33– FTIR (KBr, neat): n 3259, 2924, 1693, 1489, 1249, 842 cm
.
+
7
6
.28 (m, 2H), 7.21–7.14 (m, 2H), 6.87 (dd, J ¼ 5.0, 3.5 Hz, 1H), HRMS (ESI, m/z): [M + H] , calcd for C H ClN O : 329.1051,
1
8
18
2 2
13
.82–6.77 (m, 1H), 5.39 (s, 1H), 1.76 (s, 3H) ppm. C NMR (100 found: 329.1051.
): d 152.9, 148.5, 136.6, 131.1, 131.1, 130.8, 128.1,
4-(4-Chlorophenyl)-5-(3,4-dimethoxyphenyl)-6-methyl-3,4-
26.6, 125.3, 124.4, 107.5, 54.2, 16.3 ppm. FTIR (KBr, neat): n dihydropyrimidin-2(1H)-one (4g). 160.4 mg. Yield ¼ 89%.
MHz, DMSO-d
1
3
6
ꢁ1
ꢀ
1
244, 1686, 1490, 1389, 1247, 1091, 839, 698 cm . HRMS (ESI, Yellow solid. Mp: 151.6–152.7 C. H NMR (400 MHz, DMSO-d ):
6
+
m/z): [M + H] , calcd for C15
H
14ClN
2
OS: 305.0510, found: d 8.36 (s, 1H), 7.34–7.29 (m, 3H), 7.19–7.15 (m, 2H), 6.78 (d, J ¼
8.3 Hz, 1H), 6.63 (d, J ¼ 2.0 Hz, 1H), 6.50 (dd, J ¼ 8.2, 2.0 Hz,
305.0509.
1
3
4-(4-Chlorophenyl)-6-methyl-5-(3-(triuoromethyl)phenyl)-
1H), 5.10 (s, 1H), 3.67 (s, 3H), 3.64 (s, 3H), 1.73 (s, 3H) ppm.
C
3
,4-dihydropyrimidin-2(1H)-one (4b). 132.6 mg. Yield ¼ 72%. NMR (100 MHz, DMSO-d ): d 153.0, 148.2, 147.2, 143.4, 131.6,
6
ꢀ
1
Yellow solid. Mp: 109.8–110.4 C. H NMR (400 MHz, DMSO-d ): 130.2, 129.6, 128.8, 128.3, 121.9, 113.0, 111.4, 108.0, 58.9, 55.4,
6
d 8.60 (s, 1H), 7.51–7.42 (m, 3H), 7.40–7.31 (m, 4H), 7.23–7.14 55.3, 16.3 ppm. FTIR (KBr, neat): n 3343, 1698, 1515, 1457, 1251,
1
3
ꢁ1
+
(
m, 2H), 5.22 (s, 1H), 1.74 (s, 3H) ppm. C NMR (100 MHz, 1135, 1011, 766 cm . HRMS (ESI, m/z): [M + H] , calcd for
DMSO-d ): d 152.7, 142.9, 139.0, 133.6, 131.9, 131.7, 129.2, 129.0 C H ClN O : 359.1157, found: 359.1159.
6
1
9
20
2 3
(
2
q, J ¼ 31.3 Hz), 128.8, 128.5, 125.7 (q, J ¼ 3.8 Hz), 124.2 (q, J ¼
4-(4-Chlorophenyl)-5-(4-ethylphenyl)-6-methyl-3,4-dihy-
1
9
71.0 Hz), 123.0 (q, J ¼ 4.1 Hz), 106.6, 58.4, 16.2 ppm. F NMR dropyrimidin-2(1H)-one (4h). 146.5 mg. Yield ¼ 90%. Yellow
ꢀ
1
(
1
376 MHz, DMSO-d ): d ꢁ60.98 ppm. FTIR (KBr, neat): n 3238, solid. Mp: 229.8–231.2 C. H NMR (400 MHz, DMSO-d ): d 8.40
6
6
ꢁ1
683, 1490, 1339, 1126, 804, 704 cm . HRMS (ESI, m/z): [M + (s, 1H), 7.35–7.29 (m, 3H), 7.19–7.14 (m, 2H), 7.06 (d, J ¼ 8.2 Hz,
+
H] , calcd for C H ClF N O: 367.0820, found: 367.0822.
2H), 6.97 (d, J ¼ 8.2 Hz, 2H), 5.07 (s, 1H), 2.52 (q, J ¼ 7.6 Hz, 2H),
1
8
15
3 2
13
5-(4-Bromophenyl)-4-(4-chlorophenyl)-6-methyl-3,4-dihy-
1.73 (s, 3H), 1.12 (t, J ¼ 7.6 Hz, 3H) ppm. C NMR (100 MHz,
dropyrimidin-2(1H)-one (4c). 149.6 mg. Yield ¼ 79%. Light DMSO-d ): d 153.0, 143.2, 141.6, 135.1, 131.7, 130.1, 129.2,
6
ꢀ
1
yellow solid. Mp: 209.5–209.8 C. H NMR (400 MHz, DMSO-d
6
): 128.8, 128.4, 127.5, 107.8, 58.7, 27.7, 16.3, 15.3 ppm. FTIR (KBr,
ꢁ
1
d 8.51 (s, 1H), 7.42–7.37 (m, 3H), 7.35–7.30 (m, 2H), 7.18–7.14 neat): n 3223, 2928, 1686, 1241, 1088, 842 cm . HRMS (ESI, m/
1
3
+
(m, 2H), 7.04–7.00 (m, 2H), 5.12 (s, 1H), 1.73 (s, 3H) ppm.
C
19 20 2
z): [M + H] , calcd for C H ClN O: 327.1259, found: 327.1260.
NMR (100 MHz, DMSO-d ): d 152.8, 143.0, 137.1, 131.8, 131.5,
4-(4-Chlorophenyl)-6-ethyl-5-phenyl-3,4-dihydropyrimidin-
31.0, 130.9, 128.7, 128.4, 119.3, 106.8, 58.4, 16.2 ppm. FTIR 2(1H)-one (4i). 101.8 mg. Yield ¼ 65%. Yellow solid. Mp: 184.8–
6
1
(
ꢁ1
ꢀ
1
KBr, neat): n 3269, 1692, 1490, 1240, 1099, 844, 778 cm
.
185.7 C. H NMR (400 MHz, DMSO-d ): d 8.41 (s, 1H), 7.34–7.30
6
+
HRMS (ESI, m/z): [M + H] , calcd for C17
H
15BrClN
2
O: 377.0051, (m, 3H), 7.23 (t, J ¼ 7.4 Hz, 2H), 7.17–7.12 (m, 3H), 7.03–6.98 (m,
found: 377.0050.
2H), 5.05 (d, J ¼ 2.5 Hz, 1H), 2.04–1.94 (m, 2H), 1.03 (t, J ¼
1
3
4-(4-Chlorophenyl)-5-(4-uorophenyl)-6-methyl-3,4-dihy-
7.4 Hz, 3H) ppm. C NMR (100 MHz, DMSO-d ): d 153.2, 143.1,
6
dropyrimidin-2(1H)-one (4d). 139.5 mg. Yield ¼ 88%. Yellow 137.9, 135.5, 131.7, 129.3, 128.7, 128.4, 128.2, 126.5, 107.7, 59.0,
ꢀ
1
6
solid. Mp: 189.0–190.2 C. H NMR (400 MHz, DMSO-d ): d 8.46 22.7, 13.0 ppm. FTIR (KBr, neat): n 3235, 1679, 1489, 1227, 1091,
ꢁ
1
+
(
7
s, 1H), 7.35 (s, 1H), 7.34–7.31 (m, 2H), 7.18–7.14 (m, 2H), 7.11– 1014, 765, 701 cm . HRMS (ESI, m/z): [M + H] , calcd for
1
3
.02 (m, 4H), 5.10 (s, 1H), 1.71 (s, 3H) ppm. C NMR (100 MHz, C H ClN O: 313.1102, found: 313.1102.
18 18 2
DMSO-d ): d 160.6 (d, J ¼ 241.7 Hz), 152.8, 143.0, 134.1 (d, J ¼
Ethyl 4-(4-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydro
6
3
.3 Hz), 131.7, 131.3 (d, J ¼ 8.0 Hz), 130.4, 128.7, 128.4, 115.0 (d, pyrimidine-5-carboxylate (4j). 38.2 mg. Yield ¼ 26%. White
19
ꢀ
1
J ¼ 21.1 Hz), 107.0, 58.8, 16.2 ppm. F NMR (376 MHz, DMSO- solid. Mp: 212.3–213.6 C. H NMR (400 MHz, DMSO-d ): d 9.25
6
d
1
C
6
): d ꢁ115.91 ppm. FTIR (KBr, neat): n 3259, 1694, 1491, 1242, (s, 1H), 7.78 (s, 1H), 7.39 (d, J ¼ 8.4 Hz, 2H), 7.24 (d, J ¼ 8.4 Hz,
094, 1014, 845, 780 cm . HRMS (ESI, m/z): [M + H] , calcd for 2H), 5.14 (d, J ¼ 3.2 Hz, 1H), 3.98 (q, J ¼ 7.0 Hz, 2H), 2.24 (s, 3H),
15ClFN O: 317.0851, found: 317.0851.
ꢁ1
+
17
H
2
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RSC Adv., 2020, 10, 30062–30068 | 30067