Supplemental Information
Spectral data
4-Phenyl-6-methyl-2-oxo-N-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamide (a):
IR (KBr) cm-1: 3261, 3186 (NH), 1676 (C=O of amide).
1HNMR(300 MHz, CDCl3/DMSO-d6): δ 2.2 (3H, s, CH3-6), 5.5 (1H, s, H-4), 7.07.5 (10H, m, Ar-H), 8.0 (1H, s, N1-H), 8.1 (1H, s, NH of amide), 8.8 (1H, s, N3-H).13C-NMR
(75 MHz, CDCl3/DMSO-d6): δ 22.0, 49.2, 105.6, 119.8, 123.2, 126.2, 126.9, 127.4, 128.2,
128.4, 138.2, 143.1, 150.2, 163.7.
4-(3’-Chlorophenyl)-6-methyl-2-oxo-N-phenyl-1,2,3,4-tetrahydropyrimidine-5carboxamide (b):
IR (KBr) cm-1: 3261, 3186 (NH), 1676 (C=O of amide).
1H-NMR (300 MHz, CDCl3/DMSO-d6): δ 2.0 (3H,s,CH3-6), 5.4 (1H, s, CH-4), 6.9-7.4 (9H,
m, Ar-H), 7.8 (1H, s, N3-H), 8.6 (1H, s, N1-H), 9.3 (1H, s, NH of amide).
13C-NMR (75 MHz, CDCl3/DMSO-d6): δ 17.0, 54.8, 104.9, 119.7, 123.0, 124.6, 126.2, 127.0,
128.1,129.6, 133.4, 138.5, 138.6, 146.1, 152.7, 165.2.
4-(4’-Methoxyphenyl)-6-methyl-2-oxo-N-phenyl-1,2,3,4-tetrahydropyrimidine-5carboxamide (c):
IR (KBr) cm-1: 3261, 3186 (NH), 1676 (C=O of amide).
1H-NMR (300 MHz, CDCl3/DMSO-d6): δ 2.2 (3H, s, CH3-6), 3.7 (3H, s, OCH3), 5.1 (1H, s,
CH-4), 6.8-7.6 (9H, m, Ar-H), 7.6 (1H, s, N3-H), 9.1 (1H, s, N1-H), 9.6 (1H, s, NH of
amide).13C-NMR (75 MHz, CDCl3/DMSO-d6): δ 22.1, 52.9, 59.9, 110.7, 114.1,121.6, 125.7,
128.0, 128.9, 135.6, 146.0, 150.2, 158.6, 163.1.
4-(3’-Nitrophenyl)-6-methyl-2-oxo-N-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamide
(d):
IR (KBr) cm-1: 3261, 3186 (NH), 1676 (C=O of amide), 1325 (NO2).
1H-NMR (300 MHz, CDCl3/DMSO-d6): ): δ 2.2 (3H, s, CH3-6), 5.6 (1H, s, CH-4), 7.0-8.3
(9H, m, Ar-H), 8.7 (1H, s, N3-H), 8.9 (1H, s, N1-H), 9.4 (1H, s, NH of amide).13C-NMR (75
MHz, CDCl3/DMSO-d6): δ 22.1, 52.9, 110.7, 120.4, 121.6, 128.0 128.9, 133.2, 137.6, 144.2,
146.5, 148.0, 150.3, 163.0.
4-(3’,4’-Methylenedioxyphenyl)-6-methyl-2-oxo-N-phenyl-1,2,3,4-tetrahydro-pyrimidine-5carboxamide (e):
IR (KBr) cm-1 : 3261, 3186 (NH), 1676 (C=O of amide).
1H-NMR (300 MHz, CDCl3/DMSO-d6): ): δ 2.2 (3H, s, CH3-6), 5.1 (1H, s, CH-4), 6.0 (2H, s,
CH2), 6.6-7.6 (9H, m, Ar-H), 7.6 (1H, s, N3-H), 8.9 (1H, s, N1-H), 9.4 (1H, s, NH of
amide).13C-NMR (75 MHz, CDCl3/DMSO-d6): δ 22.1, 59.9, 101.2, 110.7, 112.0, 121.0, 121.6,
128.9, 146.8, 163.7, 170.5.
4-Phenyl-6-methyl-2-thioxo-N-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamide (f):
IR (KBr) cm-1 : 3382, 3280 (NH), 1674 (C=O of amide), 1440 (C=S).
H1-NMR (300 MHz, CDCl3/DMSO-d6): δ 2.2 (3H, s, CH3-6), 5.6 (1H, s, CH-4), 7.0-7.8 (10H,
m, Ar-H), 9.2 (1H, s, N3-H), 9.4 (1H, s, N1-H), 9.9 (1H, s, NH of amide).
13C-NMR(75MHz, CDCl3/DMSO-d6):δ 22.1, 59.9, 110.7, 121.6, 126.0, 126.9, 128.0,
128.5,128.9,137.6,159.1, 163.7, 174.1.
4-(3’-Chlorophenyl)-6-methyl-2-thioxo-N-phenyl-1,2,3,4-tetrahydro-pyrimidine-5carboxamide (g):
IR (KBr) cm-1: 3382, 3280 (NH), 1674 (C=O of amide), 1440 (C=S).
H1-NMR (300 MHz, CDCl3/DMSO-d6): δ 2.2 (3H, s, CH3-6), 5.5 (1H, s, CH-4), 7.0-7.6 (9H,
m, Ar-H), 9.3 (1H, s, N3-H), 9.6 (1H, s, N1-H), 9.8 (1H, s, NH of amide).
13C-NMR(75MHz, CDCl3/DMSO-d6): δ22.1, 59.9, 110.7, 121.6,126.0, 126.9, 128.0, 128.5,
128.9,137.6,159.1,163.7, 170.5.
4-(4’-Methoxyphenyl)-6-methyl-2-thioxo-N-phenyl-1,2,3,4- tetrahydropyrimidine-5-carboxamide (h):
IR (KBr) cm-1: 3382, 3280 (NH), 1674 (C=O of amide), 1440 (C=S).
1H-NMR (300 MHz, CDCl3/DMSO-d6): δ 2.2 (3H, s, CH3-6), 3.7 (3H, s, OCH3), 5.5 (1H, s,
CH-4), 6.8-7.8 (9H, m, Ar-H), 9.5 (1H, s, N1-H), 9.6 (1H, s, N3-H), 10.0 (1H, s, NH of amide).
13C-NMR (75 MHz, CDCl3/DMSO-d6): δ 18.5, 55.3, 108.5, 114.1, 126.2, 123.8, 128.6, 134.5,
138.8, 159.4, 165.0, 172.1.
4-(3’-Nitrophenyl)-6-methyl-2-thioxo-N-phenyl-1,2,3,4-tetrahydropyrimidine-5carboxamide (i):
IR(KBr) cm-1 : 3382, 3280 (NH), 1674 (C=O of amide), 1440 (C=S), 1326 (NO2).
1H-NMR(300 MHz, CDCl3/DMSO-d6): δ 2.5 (3H, s, CH3-6), 5.6 (1H, s, CH-4), 7.0-8.5 (9H,
m, Ar-H), 9.2 (1H, s, N3-H), 9.6 (1H, s, N1-H), 9.9 (1H, s, NH of amide).
13C-NMR(75MHz, CDCl3/DMSO-d6): δ 22.1, 59.9, 110.7, 121.6, 126.0, 126.9,128.0, 128.5,
128.9, 137.6, 144.7, 159.1, 163.7, 170.5.
4-(3’,4’-Methylenedioxyphenyl)-6-methyl-2-thioxo-N-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamide (j):
IR (KBr) cm-1 : 3382, 3280 (NH), 1674 (C=O of amide), 1440 (C=S).
1H-NMR (300 MHz, CDCl3/DMSO-d6): δ 2.0 (3H, s, CH3-6), 5.3 (1H, s, CH-4), 5.9 (2H, s,
CH2), 6.5-7.6 (9H, m, Ar-H), 8.0 (1H, s, N1-H), 8.3 (1H, s, N3-H), 9.4 (1H, s, NH of amide).
13C-NMR (75 MHz, CDCl3/DMSO-d6): δ 22.1, 59.9,101.2, 119.7, 123.0, 124.6, 126.2, 127.0,
128.1, 128.3, 129.6, 138.5, 138.6, 146.1, 152.7, 165.2.