2.4. Analytical data of selected compounds:
7-Amino-1,3-dimethyl-5-(4-nitrophenyl)-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano]2,3-d] pyrimidine-6-carbonitrile (4a) ;White solid; m.p.: 227–228 oC (Lit. m.p 227–229 oC) [36]; IR (KBr) ʋ = 3389, 3306, 3075, 2958, 2204, 1685, 1631, 1487, 1515,1382, 1230, 1186 1H NMR (400 MHz, DMSO) δ 3.10(3H, s, CH3), 3.30(3H, s, CH3), 4.50(1H, s, CH), 7.60(2H, d, J = 8 Hz, Ar-H), 8.15 (2H, d, J = 8 Hz Ar-H), 7.49(2H, s, NH2)
7-Amino-5-(4-chlorphenyl)-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]-pyrimidine-6-carbonitrile (4b) ; White Crystal; m.p.: 234–235 oC (Lit. m.p 234–237 oC) [36]; IR (KBr) ʋ = 3373, 3307, 3194, 2961, 2193, 1687, 1635, 1493, 1188, 1228, 835. 1H NMR (400 MHz, DMSO) δ 3.07 (3H, s, CH3), 3.34 (3H, s, CH3), 4.34 (1H, s, CH), 7.25–7.28 (2H, d, J = 8 Hz, Ar-H), 7.31–7.36 (2H, d, J = 8 Hz, Ar-H), 7.36 (2H, s, NH2).
7-Amino-5-(4-fluorophenyl)-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]-pyrimidine-6-carbonitrile (4c) ;White solid; m.p.: 225–226 oC (Lit. m.p 228–230 oC) [37]; IR (KBr) ʋ = 3380,3307, 3185, 2958, 2196, 1686,1636 ,1526, 1233, 1193, 857. 1H NMR (400 MHz, DMSO) δ 3.07 (3H, s, CH3), 3.34 (3H, s, CH3), 4.34 (1H, s, CH), 7.25 (2H, d, J = 8 Hz, Ar-H), 7.31 (2H, d, J = 8 Hz, Ar-H), 7.36 (2H, s, NH2).
7-Amino-5-(4-methoxyphenyl)-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H- pyrano[2,3-d]-pyrimidine-6-carbonitrile (4d) ;White solid; m.p.: 280–284 oC (Lit. m.p 280 oC) [37]; IR (KBr) ʋ = 3417,3302, 3189, 2946, 2192, 1700, 1638 ,1509, 1227, 1186, 847. 1H NMR (400 MHz, DMSO) δ 3.01 (3H, s, CH3), 3.03 (3H, s, CH3), 3.54 (3H, s, CH3), 4.30 (1H, s, CH), 6.56 (2H, d, J = 8 Hz, Ar-H), 7.15 (2H, d, J = 8 Hz, Ar-H), 7.30 (2H, s, NH2).
7-Amino-5-(4-methylphenyl)-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]-pyrimidine-6-carbonitrile (4e) ; Yellow solid; m.p.: 226–227 oC (Lit. m.p 225 oC) [37]; IR (KBr) ʋ = 3380,3310, 3200, 2923, 2199, 1687, 1640,1490, 1228, 1185, 832. 1H NMR (400 MHz, DMSO) δ 2.25 (3H, s, CH3), 3.10 (3H, s, CH3), 3.35 (3H, s, CH3), 4.25 (1H, s, CH), 7.10 (2H, d, J = 8 Hz, Ar-H), 7.10 (2H, d, J = 8 Hz, Ar-H), 7.30 (2H, s, NH2).
7-Amino-5-(3-fluorophenyl)-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]-pyrimidine-6-carbonitrile (4f) ; White solid; m.p.: 227–229 oC (Lit. m.p 228–229 oC)[38]; IR (KBr) ʋ = 3390,3314, 3197, 2965, 2201, 1688, 1642 ,1489, 1229, 1186. 1H NMR (400 MHz, DMSO) δ 3.08 (3H, s, CH3), 3.50 (3H, s, CH3), 4.50 (1H, s, CH), 7.30 (1H,d, Ar-H), 7.00(2H, s, Ar-H), 7.00 (1H, t, J = 8 Hz, Ar-H), 7.00 (1H, d, J = 8 Hz, Ar-H), 7.40 (2H, s, NH2).
7-Amino-5-(3-bromophenyl)-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]-pyrimidine-6-carbonitrile (4g) ; White solid; m.p.: 216–218 oC (Lit. m.p: 218–219 oC) [39]; IR (KBr) ʋ = 3377,3313, 3197, 2960, 2202, 1684, 1638 ,1490, 1228, 1186, 1071. 1H NMR (400 MHz, DMSO) δ 3.02 (3H, s, CH3), 3.34 (3H, s, CH3), 4.34 (1H, s, CH), 7.25 (2H, m, Ar-H), 7.40 (1H, m, Ar-H), 7.42 (2H, s, NH2).
7-Amino-5-(3-methoxyphenyl)-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]-pyrimidine-6-carbonitrile (4h) ; White solid; m.p.: 200–206 oC (Lit. m.p: 200–206 oC) [7]; IR (KBr) ʋ = 3407,3318, 3199, 2951, 2193, 1688, 1649 ,1494, 1229, 1187, 746. 1H NMR (400 MHz, DMSO) δ 3.08(3H, s, CH3), 3.34(3H, s, CH3), 3.72(3H, s, CH3), 4.30(1H, s, CH), 6.72 (1H, s, Ar-H), 6.78(2H, d, J = 8 Hz, Ar-H), 7.20(1H, t, J = 8 Hz, Ar-H), 7.32(2H, s, NH2).
7-Amino-1,3-dimethyl-5-(3-nitrophenyl)-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano]2,3-d]-pyrimidine-6-carbonitrile (4i) ;White solid; m.p.: 255 − 226 oC (Lit. m.p 255 − 227 oC) [37]; IR (KBr) ʋ = 3430, 3333, 3185, 2952, 2195, 1695, 1650, 1492, 1520,1389, 1231, 1188, 677, 776, 904. 1H NMR (400 MHz, DMSO) δ 3.06 (3H, s, CH3), 3.36 (3H, s, CH3), 4.56 (1H, s, CH), 7.32 (2H, s, NH2), 7.60 (1H, t, J = 8 Hz, Ar-H), 7.78 (1H, d, J = 8 Hz, Ar-H), 8.10 (1H, d, J = 8 Hz, Ar-H), 8.10 (1H, s, Ar-H).
7-Amino-5-(2-bromophenyl)-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]-pyrimidine-6-carbonitrile (4j) ;white solid; m.p.: 237 oC (Lit. m.p: 237–238 oC) [38]; IR (KBr) ʋ = 3397, 3311, 3190, 2960, 2194, 1688, 1643 ,1489, 1232, 1190, 1071. 1H NMR (400 MHz, DMSO) δ 3.04 (3H, s, CH3), 3.34 (3H, s, CH3), 4.86 (1H, s, CH), 7.12 (1H, m, J = 8 Hz, Ar-H), 7.25 (1H, d, J = 8 Hz, Ar-H), 7.26 (1H, t, J = 8 Hz, Ar-H), 7.52 (1H, d, J = 8 Hz, Ar-H), 7.42 (2H, s, NH2).
7-Amino-5-(2-fluorophenyl)-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]-pyrimidine-6-carbonitrile (4k) ;White solid; m.p.: 237–239 oC (Lit. m.p: 238–239 oC) [38]; IR (KBr) ʋ = 3380, 3308, 3185, 2959, 2197, 1689, 1639 ,1497, 1233, 1193, 748. 1H NMR (400 MHz, DMSO) δ 3.05 (3H, s, CH3), 3.35 (3H, s, CH3), 4.70 (1H, s, CH), 7.10 (1H, t, J = 8 Ar-H), 7.1 (1H, d, J = 8 Hz, Ar-H), 7.25 (1H, d, J = 8 Hz, Ar-H), 7.25 (1H, t, J = 8 Hz, Ar-H) 7.40 (2H, s, NH2).
7-Amino-5-(2-methylphenyl)-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]-pyrimidine-6-carbonitrile (4l) ;White solid; m.p.: 247 oC (Lit. m.p: 247–248 oC) [40]; IR (KBr) ʋ = 3379, 3312, 3197, 2958, 2200, 1712, 1687, 1488, 1228, 1185, 751. 1H NMR (400 MHz, DMSO) δ 2.26 (3H, s, CH3), 3.06 (3H, s, CH3), 3.34 (3H, s, CH3), 4.26 (1H, s, CH), 7.00 (3H, m, Hz, Ar-H), 7.16 (1H, t, J = 8 Hz, Ar-H), 7.30 (2H, s, NH2).
7-Amino-5-(2-chlorphenyl)-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]-pyrimidine-6-carbonitrile (4m) ;White solid; m.p.: 238–240 oC (Lit. m.p: 238–240 oC) [41]; IR (KBr) ʋ =3395, 3312, 3192, 2957, 2194, 1689, 1642, 1487, 1232, 1190, 751. 1H NMR (400 MHz, DMSO) δ 3.05 (3H, s, CH3), 3.35 (3H, s, CH3), 4.85 (1H, s, CH), 7.20 (4H, t, J = 8 Hz, Ar-H), 7.30 (2H, d, J = 8 Hz, Ar-H), 7.29–7.38 (2H, d, J = 8 Hz Ar-H), 7.35 (2H, s, NH2).
7-Amino-1,3-dimethyl-5-(2-nitrophenyl)-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano]2,3-d]-pyrimidine-6-carbonitrile (4n) ;White solid; m.p.: 213–215 oC (Lit. m.p 216 oC) [41]; IR (KBr) ʋ = 3381, 3307, 3185, 2952, 2196, 1687, 1636, 1496, 1526,1354, 1233, 1193, 747. 1H NMR (400 MHz, DMSO) δ 3.00 (3H, s, CH3), 3.31(3H, s, CH3), 5.15 (1H, s, CH), 7.42 (1H, t, J = 8 Hz, Ar-H), 7.51(1H, d, J = 8 Hz Ar-H), 7.62 (1H, d, J = 8 Hz Ar-H), 7.82 (1H, d, J = 8 Hz Ar-H), 7.50 (2H, s, NH2).
7-Amino-5-(2,6-dichlorophenyl)-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]-pyrimidine-6-carbonitrile (4o) ;White solid; m.p.: 243–244 oC (Lit. m.p 243–244 oC) [43]; IR (KBr) ʋ = 3385, 3314, 3192, 3196, 2199, 1690, 1655 ,1461, 1235, 1037, 755. 1H NMR (400 MHz, DMSO) δ 3.04 (3H, s, CH3), 3.34 (3H, s, CH3), 5.38 (1H, s, CH), 7.26 (1H, t, J = 8 Hz, Ar-H), 7.34 (1H, d, J = 8 Hz, Ar-H), 7.46 (1H, d, J = 8 Hz, Ar-H) 7.46 (2H, s, NH2).
7-Amino-5-(2,4-dichlorophenyl)-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]-pyrimidine-6-carbonitrile (4p) ;White solid; m.p.: 243–245 oC (Lit. m.p 243–246 oC) [43]; IR (KBr) ʋ = 3391, 3310, 3192, 2960, 2195, 1690, 1640,1461, 1228, 1186. 1H NMR (400 MHz, DMSO) δ 3.02 (3H, s, CH3), 3.34 (3H, s, CH3), 4.84 (1H, s, CH), 7.32–7.38 (2H, m, Ar-H), 7.41 (1H, s, Ar-H), 7.41(2H, s, NH2).
7-Amino-5-(3,4,5-trimethoxyphenyl)-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]-pyrimidine-6-carbonitrile (4q) ; Yellow solid; m.p.: 177 oC ; IR (KBr) ʋ = 3342, 3191, 2945, 2197, 1694, 1648, 1496, 1184, 1119. 1H NMR (400 MHz, DMSO) δ 3.10 (3H, s, CH3), 3.35 (3H, s, CH3), 3.60 (3H, s, CH3), 3.70 (6H, s, CH3), 4.30 (1H, s, CH), 6.50 (2H, s, Ar-H),), 7.30 (2H, s, NH2).
7-Amino-1,3-dimethyl-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]-pyrimidine-6-carbonitrile (4r) ;White solid; m.p.: 259–260 oC (Lit. m.p 260–262 oC) [44]; IR (KBr) ʋ = 3374, 3308, 3194, 2961, 2194, 1688, 1636,1493, 1229, 1188.1H NMR (400 MHz, DMSO) δ 3.07 (3H, s, CH3), 3.35 (3H, s, CH3), 4.31(1H, s, CH), 7.20 (5H, m, Hz Ar-H), 7.32 (2H, s, NH2).