Journal of Chemistry

Research Article

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

Table 2

Spectral data of 6-substituted-pyrimidine derivatives (4a, b and 5a–f).


Compd.	MS (m/e M⁺)	IR (KBr) ν (cm⁻¹)	¹H-NMR^a (CDCl₃) δ (ppm)

4a	264(98), 235(100), 209(30), 70(8).	2204 (C≡N)	2.30–2.11 (4H, m, 3,4-H of pyrrolidinyl), 2.82 (3H, s, CH₃), 4.09 (2H, t, J = 1.40 Hz, 5-H of pyrrolidinyl), 4.21 (2H, t, J = 1.40 Hz, 2-H of pyrrolidinyl), 8.08–8.07, 7.76–7.57 (5H, m, phenyl-H).
4b	278(100), 263(7), 249(92), 236(26), 223(24), 210(8), 196(12), 154(30), 104(42), 77(17), 55(3).	2208 (C≡N)	1.76, 4.02 (10H, m, piperidinyl-H), 2.69 (3H, s, CH₃), 8.41–8.39, 7.50–7.45 (5H, m, phenyl-H).
5a	280(100), 249(32), 236(17), 223(91), 194(16), 153(46), 125(4), 104 (37), 77(24), 56(7).	2210 (C≡N)	2.69 (3H, s, CH₃), 3.85 (4H, d, J = 1.0 Hz, 2,6-H of morpholinyl), 4.07 (4H, d, J = 1.0 Hz, 3,5-H of morpholinyl), 8.40–8.38, 7.52–7.45 (5H, m, phenyl-H).
5b	293(9), 249(4), 236(19), 223(100), 194(4), 153(11), 104(14), 83(46), 70(43), 55(7).	2205 (C≡N)	2.43 (3H, s, CH₃), 2.68 (3H, s, N-CH₃), 2.66 (4H, d, J = 1.0 Hz, 2,6-H of piperazinyl), 4.14 (4H, d, J = 1.0 Hz, 3,5-H of piperazinyl), 8.40–8.38, 7.50–7.45 (5H, m, phenyl-H).
5c	307(12), 263(4), 249(5), 236(29), 223(65), 194(4), 153(11), 104(12), 97(60), 84(100), 72(14), 55(7).	2206 (C≡N)	1.14 (3H, t, J = 1.44 Hz, N-CH₂CH ₃), 2.67 (3H, s, CH₃), 2.51 (2H, q, J = 2.16 Hz, N-CH ₂CH3), 2.62 (4H, d, J = 1.0 Hz, 2,6-H of piperazinyl), 4.11 (4H, d, J = 1.0 Hz, 3,5-H of piperazinyl), 8.40–8.38, 7.50–7.44 (5H, m, phenyl-H).
5d	351(95), 336(1), 322(8), 306(2), 283(17), 278(2), 249(9), 236(382), 223(100), 194(6), 153(1), 141(10), 58(4).	1705 (C=O) 2207 (C≡N)	1.30 (3H, t, J = 1.43 Hz, OCH₂CH ₃), 2.69 (3H, s, CH₃), 3.67 (4H, t, J = 1.06 Hz, 2,6-H of piperazinyl), 4.05 (4H, d, J = 1.00 Hz, 3,5-H of piperazinyl), 4.20 (2H, q, J = 2.13 Hz, COOCH₂), 8.40–8.38, 7.53–7.45 (5H, m, phenyl-H).
5e	355(42), 249(5), 236(28), 223(100), 194(3), 177(4), 153(10), 132(94), 120(31), 104(44), 77(20), 55(5).	2200 (C≡N)	2.70 (3H, s, CH₃), 3.37 (4H, d, J = 1.09 Hz, 2,6-H of piperazinyl), 4.25 (4H, d, J = 1.00 Hz, 3,5-H of piperazinyl), 8.43–8.42, 7.52–6.91 (10H, m, phenyl-H).
5f	357(57), 262(9), 249(15), 236(34), 223(100), 194(5), 179(6), 153(11), 147(44), 134(67), 123(24), 108(39), 103(16), 80(22), 55(5).	2204 (C≡N)	2.69 (3H, s, CH₃), 4.02 (4H, d, J = 1.06 Hz, 2,6-H of piperazinyl), 4.16 (4H, d, J = 1.06 Hz, 3,5-H of piperazinyl), 6.56 (1H, m, 5-H of pyrimidinyl), 8.36 (2H, d, J = 1.0 Hz, 4,6-H of pyrimidinyl), 8.42–8.40, 7.51–7.45 (5H, m, phenyl-H).

Abbreviations: s, singlet; d, doublet; t, triplet; q, quartet; m, multiplet.