M. Soleymani – H. R. Memarian · Synthesis of 3,4-Dihydropyrimidin-2(1H)-one-5-carboxamides
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6-Methyl-2-(1H)-oxo-4-phenyl-3,4-dihydropyrimidine-5-
6-Methyl-2-(1H)-oxo-4-(3-chlorophenyl)-3,4-dihydropyr-
imidine-5-(2ꢀ-chlorophenyl)carboxamide (10)
(4ꢀ-bromophenyl)carboxamide (7)
One recrystallization. M. p.: 188 – 190 ◦C. – IR: ν = 3400,
3300 (N-H), 1710 (CONH), 1645 (CO), 1600 cm−1. –1H
NMR (300 MHz, [D6]DMSO): δ = 2.16 (s, 3H, CH3), 5.38
(br s, 1H, pyrimidine-4H), 7.15 – 7.45 (several multiplets,
8H, aromatic H), 7.70 (s, 1H, 1-NH), 8.88 (s, 1H, 3-NH),
9.18 (s, 1H, HNAr). – 13C NMR (75.48 MHz, [D6]DMSO):
δ = 17.80, 54.98, 104.08, 125.64, 126.93, 127.10, 127.64,
127.75, 127.83, 128.69, 129.87, 130.92, 133.54, 135.60,
141.15, 146.88, 152.80, 165.60. – MS (EI, 70 eV): m/z (%) =
377 (4), 221 (3), 156 (12), 155 (9), 154 (9), 153 (5), 140 (12),
138 (7), 129 (5), 128 (4), 127 (18), 126 (11), 113 (11), 111
(28), 76 (52). – UV (EtOH): λmax(logεmax) = 285.5 (3.80),
206.5 nm (4.22). – C18H15Cl2N3O2 (376.2): calcd. C 57.46,
H 4.02, N 11.17; found C 57.53, H 4.20, N 11.18.
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Two times recrystallized. M. p.: 269 – 270 C. – IR: ν =
3240 (N-H), 1705 (CONH), 1675 (CO), 1625 cm−1. – 1H
NMR (300 MHz, [D6]DMSO): δ = 2.03 (s, 3H, CH3), 5.40
(br s, 1H, pyrimidine-4H), 7.22 – 7.54 (several multiplets,
9H, aromatic H), 7.63 (s, 1H, 1-NH), 8.78 (s, 1H, 3-NH),
9.69 (s, 1H, HNAr). – 13C NMR (75.48 MHz, [D6]DMSO):
δ = 17.54, 55.40, 105.59, 115.09, 121.88, 126.64, 127.80,
128.95, 131.77, 139.07, 139.51, 144.73, 153.01, 165.85. –
MS (EI, 70 eV): m/z (%) = 215 (10), 199 (7), 197 (4), 187 (5),
173 (10), 172 (16), 171 (9), 170 (9), 105 (11), 104 (21), 77
(89), 76 (30). – UV (EtOH): λmax(logεmax) = 286.0 (4.16),
206.0 nm (4.37). – C18H16BrN3O2 (386.2): calcd. C 55.97,
H 4.18, N 10.88; found C 55.95, H 4.52, N 10.53.
6-Methyl-2-(1H)-oxo-4-phenyl-3,4-dihydropyrimidine-5-
6-Methyl-2-(1H)-oxo-4-(4-chlorophenyl)-3,4-dihydropyr-
(4ꢀ-methoxyphenyl)carboxamide (8)
imidine-5-(2ꢀ-chlorophenyl)carboxamide (11)
Prepara◦tive layer chromatography (ethyl acetate). M. p.:
241 – 243 C. – IR: ν = 3250 (N-H), 1710 (CONH), 1675
(CO), 1625 cm−1. – 1H NMR (300 MHz, [D6]DMSO):
δ = 2.04 (s, 3H, CH3), 3.69 (s, 3H, OCH3), 5.40 (br s,
1H, pyrimidine-4H), 6.81 – 7.46 (several multiplets, 9H, aro-
matic H), 7.56 (s, 1H, 1-NH), 8.68 (s, 1H, 3-NH), 9.43 (s,
1H, HNAr). – 13C NMR (75.48 MHz, [D6]DMSO): δ =
17.46, 55.54, 55.59, 106.00, 114.10, 121.64, 126.70, 127.75,
128.91, 132.79, 138.30, 144.79, 153.16, 155.63, 165.38. –
MS (EI, 70 eV): m/z (%) = 337 (3), 215 (4), 149 (10),
123 (32), 122 (77), 105 (18), 77 (100), 76 (34). – UV
(EtOH): λmax(logεmax) = 284.4 (4.34), 212.4 nm (4.13). –
C19H19N3O3 (337.4): calcd. C 67.64, H 5.68, N 12.46; found
C 67.14, H 5.66, N 12.04.
One recrystallization. M. p.: 245 – 247 ◦C. – IR: ν = 3210
1
(N-H), 1700 (CONH), 1660 (CO), 1620 cm−1. – H NMR
(300 MHz, [D6]DMSO): δ = 2.16 (s, 3H, CH3), 5.38 (br
s, 1H, pyrimidine-4H), 7.16 – 7.41 (several multiplets, 8H,
aromatic H), 7.69 (s, 1H, 1-NH), 8.87 (s, 1H, 3-NH), 9.12
(s, 1H, HNAr). – 13C NMR (75.48 MHz, [D6]DMSO):
δ = 17.76, 54.86, 104.26, 127.00, 127.48, 127.74, 128.48,
128.90, 129.84, 132.43, 135.58, 140.92, 143.39, 152.79,
165.61. – MS (EI, 70 eV): m/z (%) = 223 (2), 221 (9), 168 (3),
166 (3), 156 (4), 155 (4), 154 (10), 153 (7), 140 (4), 139 (3),
138 (7), 129 (8), 128 (11), 127 (23), 126 (17), 113 (15), 111
(66), 76 (32). – UV (EtOH): λmax(logεmax) = 275.0 (4.11),
205.0 nm (4.24). – C18H15Cl2N3O2 (376.2): calcd. C 57.46,
H 4.02, N 11.17; found C 57.33, H 4.12, N 11.15.
6-Methyl-2-(1H)-oxo-4-(2-chlorophenyl)-3,4-dihydropyr-
6-Methyl-2-(1H)-oxo-4-(2-bromophenyl)-3,4-dihydropyr-
imidine-5-(2ꢀ-chlorophenyl)carboxamide (9)
imidine-5-(2ꢀ-chlorophenyl)carboxamide (12)
One recrystallization. M. p.: 245 – 247 ◦C. – IR: ν = 3205,
One recrystallization. M. p.: 221 – 223 ◦C. – IR: ν = 3200,
3095 (N-H), 1705 (CONH), 1650 (CO), 1590 cm−1. – 1H 3100 (N-H), 1705 (CONH), 1650 (CO), 1590 cm−1. – 1H
NMR (300 MHz, [D6]DMSO): δ = 2.17 (s, 3H, CH3), 5.77 NMR (300 MHz, [D6]DMSO): δ = 2.17 (s, 3H, CH3), 5.73
(br s, 1H, pyrimidine-4H), 7.11 – 7.50 (several multiplets, (br s, 1H, pyrimidine-4H), 7.11 – 7.56 (several multiplets,
8H, aromatic H), 7.52 (s, 1H, 1-NH), 8.89 (s, 1H, 3-NH), 8H, aromatic H), 7.58 (s, 1H, 1-NH), 8.90 (s, 1H, 3-NH),
9.10 (s, 1H, HNAr). – 13C NMR (75.48 MHz, [D6]DMSO): 9.10 (s, 1H, HNAr). – 13C NMR (75.48 MHz, [D6]DMSO):
δ = 17.63, 53.24, 103.76, 126.82, 126.91, 127.73, 127.97, δ = 17.63, 55.71, 104.12, 122.78, 126.86, 127.74, 127.90,
128.11, 129.75, 129.82, 129.90, 129.98, 132.33, 135.54, 128.79, 129.83, 130.11, 133.21, 135.49, 140.22, 142.63,
140.47, 141.00, 152.50, 165.48. – MS (EI, 70 eV): m/z (%) = 152.37, 165.48. – MS (EI, 70 eV): m/z (%) = 342 (6), 341
377 (2), 375 (4), 340 (10), 249 (78), 222 (2), 221 (13), 156 (4), 340 (19), 293 (28), 267 (6), 265 (7), 185 (23), 184
(5), 155 (6), 154 (7), 153 (9), 141 (10), 140 (22), 139 (25), (13), 183 (15), 182 (8), 157 (15), 156 (9), 155 (16), 154
138 (33), 129 (32), 128 (27), 127 (100), 126 (26), 113 (16), (7), 129 (37), 128 (34), 127 (96), 126 (20), 76 (55). – UV
111 (49), 76 (24). – UV (EtOH): λmax(logεmax) = 289.0 (EtOH): λmax(logεmax) = 279.0 (4.27), 209.0 nm (4.53). –
(3.84), 206.0 nm (4.33). – C18H15Cl2N3O2 (376.2): calcd. C18H15BrClN3O2 (420.7): calcd. C 51.39, H 3.59, N 9.99;
C 57.46, H 4.02, N 11.17; found C 57.22, H 3.99, N 11.17.
found C 51.11, H 3.60, N 9.72.
Unauthenticated
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