Journal of Chemistry

Research Article

Thioxopyrimidine in Heterocyclic Synthesis I: Synthesis of Some Novel 6-(Heteroatom-substituted)-(thio)pyrimidine Derivatives

Table 7

Spectral data of 6-[(4,5,6-trisubstituted-2-phenyl-pyridin-3-yl)thio]-5-cyano-4-methyl-2-phenyl-pyrimidine derivatives (16a–f).


Compd.	MS (m/e M⁺)	IR (KBr) ν (cm⁻¹)	¹H-NMR^a (CF₃COOD) δ (ppm)

16a	456(6), 354(48), 344(100), 328(1), 268(3), 251(15), 236(1), 186(2), 105(3).	2203 (C≡N)	3.67 (3H, s, CH₃), 8.44 (1H, d, J = 1.01 Hz, 5-H of pyridyl), 8.76 (1H, d, J = 1.01 Hz, 4-H of pyridyl), 8.54–8.52, 8.19–7.87 (15H, m, phenyl-H).
16b	462(5), 435(10), 430(6), 354(18), 344(100), 268(2), 251(6), 185(3), 171(4), 143(7), 129(3).	2206 (C≡N)	3.63 (3H, s, CH₃), 8.36 (1H, d, J = 1.00 Hz, 5-H of pyridyl), 8.68 (1H, d, J = 1.00 Hz, 4-H of pyridyl), 8.20 (1H, d, J = 1.00 Hz, 3-H of thienyl-H),, 8.45 (1H, d, J = 1.00 Hz, 5-H of thienyl-H), 8.47–8.45, 8.13–7.80 (11H, m, 4-H of thienyl-H and phenyl-H).
16c	457(4), 430(9), 368(3), 354(100), 344(90), 303(8), 268(20), 251(45), 201(3), 186(7), 105(10).	2208 (C≡N)	3.08 (3H, s, CH₃), 7.99 (1H, d, J = 1.00 Hz, 4-H of pyridyl), 8.15 (1H, d, J = 1.00 Hz, 4-H of S-pyridyl), 8.25–8.23, 7.90–7.58 (12H, m, 5-H of S-pyridyl, 5-H of pyridyl and phenyl-H), 8.47 (1H, d, J = 1.00 Hz, 6-H of pyridyl), 9.79 (1H, s, 2-H of pyridyl).
16d	481(4), 454(28), 430(55), 378(4), 354(100), 347(86), 303(20), 267(46), 201(4), 137(14) 105(21), 77(4).	2210 (C≡N)	3.02 (3H, s, CH₃), 8.55 (1H, s, 4-H of pyridyl), 8.32–8.30, 7.79–7.65 (15H, m, phenyl-H).
16e	476(5), 430(10), 368(55), 344(100), 327(4), 268(8), 265(18), 201(2), 105(2).	2206 (C≡N)	2.30 (3H, s, CH₃), 3.38 (3H, s, CH₃), 7.81 (1H, s, 5-H of pyridyl), 8.04 (1H, dd, J = 1.53, 1.51 Hz, 4-H of thienyl-H), 8.15 (1H, d, J = 1.00, Hz, 3-H of thienyl-H), 8.52 (1H, d, J = 1.00, Hz, 5-H of thienyl-H), 8.32–8.30, 7.93–7.65 (10H, m, phenyl-H).
16f	498(5), 430(3), 368(7), 344(100), 268(5), 201(2), 105(2), 77(2).	1688 (C=O) 2207 (C≡N)	2.32 (3H, s, CH₃), 2.82 (3H, s, CH₃), 8.84 (1H, s, 4-H of pyridyl), 8.41–8.36, 8.30–8.17 (15H, m, phenyl-H).

Abbreviations: s: singlet; d: doublet; m: multiplet.