SYNTHESIS, CHARACTERIZATION, AND in vitro ANTIBACTERIAL EVALUATION
863
1
(
C=O), 1217 (C–N), 1516, 1420 (C=C). H NMR
3302 (N–H), 1237 (C–N), 1421 (C=C), 1055 (C–O).
H NMR spectrum, δ, ppm: 6.56–6.72 m (1H), 7.17–
1
spectrum, δ, ppm: 5.67–5.70 s (1H), 6.87–6.89 d (1H),
7
7
3
8
2
1
.53–7.58 d (1H), 8.16 s (1H), 7.45–7.48 m (1H),
.53–7.55 m (1H), 8.20–8.33 d (1H), 6.22 s (1H),
.17 s (6H), 3.22 s (6H), 3.35 s (6H), 9.83 s (1H),
7.25 d (1H), 7.26–7.29 d (1H), 5.65 s (2H), 6.23 s
(1H), 3.18 s (6H), 3.52 s (6H), 3.56 s (6H), 8.33 s
1
3
(1H), 8.47 s (1H). C NMR spectrum, δ , ppm: 28.19,
C
1
3
.44 s (1H). C NMR spectrum, δ , ppm: 28.85,
29.84, 35.17, 39.39, 89.63, 127.46, 130.64, 136.91,
142.98, 152.11, 162.97. Mass spectrum: m/z 458.19.
C
9.36, 34.18, 39.79, 89.92, 127.33, 128.26, 128.36,
28.37, 130.61, 136.75, 142.87, 151.38, 161.95. Mass
5
,5′-[(4-Methoxyphenyl)methylene]bis[1,3-di-
spectrum: m/z 492.
methyl-6-(methylamino)pyrimidine-2,4(1H,3H)-di-
one] (3k). Yield 86%, yellow solid, mp 120°C,
5
,5′-[(4-Chlorophenyl)methylene]bis[1,3-di-
–
1
methyl-6-(methylamino)pyrimidine-2,4(1H,3H)-di-
one] (3g). Yield 74%, light brown solid, mp 155°C,
R 0.583. IR spectrum, ν, cm : 3392 (N–H), 3001
R 0.58. IR spectrum, ν, cm : 3321 (N–H), 3121
f
(=C–H), 2921, 2926 (–C–H), 1642 (C=O), 1237
–
1
1
(C–N), 1429 (C=C), 1140 (C–O). H NMR spectrum,
f
(
(
8
7
=C–H), 2930 (–C–H), 1671 (C=O), 1217 (C–N), 1413
C=C), 670 (C–Cl). H NMR spectrum, δ, ppm: 8.02–
δ, ppm: 6.82–6.89 d (1H), 6.90–6.99 d (1H), 7.25–
7.32 d (1H), 7.34–7.39 d (1H), 6.03 s (1H), 3.28 s
(6H), 3.36 s (6H), 3.64 s (6H), 8.45 s (1H), 8.48 s
1
.04 d (1H), 7.52–7.54 d (1H), 7.18–7.20 d (1H),
.05–7.07 d (1H), 6.13 s (1H), 3.28 s (6H), 3.17 s
1
3
(1H). C NMR spectrum, δ , ppm: 26.19, 28.34,
C
1
3
(
6H), 10 s (1H), 3.275 s (6H), 8.31 s (1H). C NMR
35.07, 39.19, 89.23, 127.70, 130.65, 136.81, 142.19,
spectrum, δ , ppm: 27.99, 28.58, 33.07, 38.89, 90.75,
150.37, 162.86. Mass spectrum: m/z 456.21.
C
1
27.38, 131.13, 136.65, 142.84, 151.02, 161.95. Mass
spectrum: m/z 459.23.
,5′-[(4-Fluorophenyl)methylene]bis[1,3-di-
5
,5′-[(4-Hydroxy-3-methoxyphenyl)methylene]-
bis[1,3-dimethyl-6-(methylamino)pyrimidine-
2,4(1H,3H)-dione] (3l). Yield 78%, creamish yellow
solid, mp 190°C, R 0.58. IR spectrum, ν, cm : 3516
(O–H), 3331 (N–H), 3115 (=C–H), 2912, 2926 (C–H),
1630 (C=O), 1237 (C–N), 1433 (C=C), 1062, 1140
(C–O). H NMR spectrum, δ, ppm: 5.65 s (1H), 6.77 s
(1H), 6.82–6.88 d (1H), 6.90–6.92 d (1H), 6.06 s (1H),
3.76 s (3H), 3.40 s (6H), 3.52 s (6H), 3.68 s (6H),
5
–
1
methyl-6-(methylamino)pyrimidine-2,4(1H,3H)-di-
one] (3h). Yield 88%, light brown solid, mp 145°C,
R 0.56. IR spectrum, ν, cm : 3321 (N–H), 3121
f
–
1
f
1
(
(
=C–H), 2921 (–C–H), 1642 (C=O), 1237 (C–N), 1429
C=C), 1213 (C–F). H NMR spectrum, δ, ppm: 7.16–
1
7
7
.33 d (1H), 7.12–7.16 d (1H), 7.35–7.52 d (1H),
.54–7.59 d (1H), 6.13 s (1H), 3.185 s (6H), 3.33 s
13
8.29 s (1H), 8.31 s (1H). C NMR spectrum, δ , ppm:
C
1
3
(
6H), 3.345 s (6H), 8.43 s (1H), 8.24 s (1H). C NMR
27.89, 29.76, 36.47, 39.39, 89.26, 127.48, 130.74,
135.81, 143.88, 152.76, 162.84. Mass spectrum:
m/z 472.
spectrum, δ , ppm: 26.89, 29.34, 36.07, 39.39, 89.67,
C
1
27.47, 130.63, 136.91, 142.99, 150.07, 162.96. Mass
spectrum: m/z 444.19.
,5′-[(4-Nitrophenyl)methylene]bis[1,3-dimethyl-
-(methylamino)pyrimidine-2,4(1H,3H)-dione] (3i).
Yield 83%, light yellow solid, mp 210°C, R 0.423. IR
5
,5′-[(3-Hydroxy-4-methoxyphenyl)methylene]-
5
bis[1,3-dimethyl-6-(methylamino)pyrimidine-
2,4(1H,3H)-dione] (3m). Yield 76%, yellow solid,
mp 210°C, R 0.56. IR spectrum, ν, cm : 3520, 3516
(O–H), 3112 (=C–H), 2910, 2924 (–C–H), 1630
(C=O), 3330 (N–H), 1237 (C–N), 1430 (C=C), 1060,
6
–
1
f
f
–
1
spectrum, ν, cm : 3341 (N–H), 3011 (=C–H), 2901
–C–H), 1651 (C=O), 1543, 1303 (NO ), 1247 (C–N),
(
1
2
1
1
431 (C=C). H NMR spectrum, δ, ppm: 8.16–8.32 d
1130 (C–O). H NMR spectrum, δ, ppm: 5.65 s (1H),
(
(
(
1H), 8.27–8.29 d (1H), 7.26–7.32 d (1H), 7.19–7.28 d
1H), 6.22 s (1H), 3.28 s (6H), 3.32 s (6H), 3.42 s
6.77–6.79 d (1H), 6.80–6.88 d (1H), 6.84 s (1H),
6.20 s (1H), 3.78 s (3H), 3.22 s (6H), 3.52 s (6H),
3.69 s (6H), 8.19 s (1H), 8.21 s (1H). C NMR spec-
1
3
13
6H), 8.23 s (1H), 8.14 s (1H). C NMR spectrum, δ ,
C
ppm: 24.89, 29.14, 35.07, 39.29, 90.23, 127.26,
29.53, 136.89, 142.97, 150.06, 162.95, 163.99. Mass
spectrum: m/z 471.19.
,5′-[(3,4-Dihydroxyphenyl)methylene]-
bis[1,3-dimethyl-6-(methylamino)pyrimidine-
,4(1H,3H)-dione] (3j). Yield 82%, orange yellow
trum, δ , ppm: 28.99, 29.96, 36.97, 39.42, 90.29,
127.28, 130.64, 135.91, 143.98, 152.96, 162.74. Mass
spectrum: m/z 472.21.
C
1
5
5,5′-(Naphthalen-1-ylmethylene)bis[1,3-di-
methyl-6-(methylamino)pyrimidine-2,4(1H,3H)-di-
2
one] (3n). Yield 70%, brownish yellow solid,
–
1
–1
solid, mp 230°C, R 0.56. IR spectrum, ν, cm : 3520,
mp >250°C, R 0.53. IR spectrum, ν, cm : 3352
f
f
3
555 (O–H), 3101 (=C–H), 2911 (–C–H), 1660 (C=O),
(N–H), 3011 (=C–H), 2901 (–C–H), 1651 (C=O), 1207
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 55 No. 6 2019