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Chapter 2<br />
Synthesis of substituted pyrimidines via Wittig<br />
5-((E)-(4-nitrostyryl))-2-chloro-4-(4-fluorophenyl)-6-isopropylpyrimidine (AW-<br />
02). Yellow solid; R f 0.72 (8:2 hexane-EtOAc); mp 110-112 ° C; IR (KBr): 3077, 3065,<br />
3031, 2932, 2856, 1664, 1450, 1430, 1368, 830 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ<br />
1.34-1.36 (d, 6H, 2 x i prCH 3 ), 3.44-3.49 (m, 1H, i prCH), 6.55-6.61 (d, 1H, j=16.5Hz,<br />
ethylene-H), 7.08-7.17 (m, 3H, Ar-H & ethylene-H), 7.48-7.51 (d, 2H, Ar-H), 7.64-<br />
7.68 (t, 2H, Ar-H), 8.19-8.22 (d, 2H, Ar-H); 13 C NMR (DEPT):(75 MHz, CDCl 3 ):<br />
21.73, 32.38, 115.48, 115.77, 124.29, 126.16, 127.09, 132.00, 132.11, 135.01; MS<br />
(m/z): 398 (M + ); Anal. Calcd for C 21 H 17 ClFN 3 O 2 : C, 63.40; H, 4.31; N, 10.56; Found:<br />
C, 63.43; H, 4.37; N, 10.50.<br />
5-((E)-(4-chlorostyryl))-2-chloro-4-(4-fluorophenyl)-6-isopropylpyrimidine (AW-<br />
03). White solid; R f 0.65 (8:2 hexane-EtOAc); mp 56-58 ° C; IR (KBr): 3095, 3084,<br />
3035, 2938, 2850, 1668, 1434, 1434, 1373, 830 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ<br />
1.32-1.34 (d, 6H, 2 x i prCH 3 ), 3.45-3.50 (m, 1H, i prCH), 6.43-6.49 (d, 1H, j=16.5Hz,<br />
ethylene-H), 6.88-6.93 (d, 1H, j=16.5Hz, ethylene-H), 7.05 -7.11 (t, 2H, Ar-H), 7.26-<br />
7.38 (q, 4H, Ar-H), 7.64-7.69 (t, 2H, Ar-H); 13 C NMR(DEPT):(75 MHz, CDCl 3 ):<br />
21.47, 32.19, 115.33, 115.62, 122.00, 127.71, 129.09, 132.01, 132.12, 136.01;MS<br />
(m/z): 388 (M + ); Anal. Calcd for C 21 H 17 Cl 2 FN 2 : C, 65.13; H, 4.42; N, 7.23; Found: C,<br />
65.23; H, 4.37; N, 7.35.<br />
2-Choloro-4-(4-flurophenyl)-6-isopropyl-5-[(E)-2-(thiophene-2-yl)vinyl]-<br />
pyrimidine (AW-04). White solid; R f 0.79 (8:2 hexane-EtOAc); mp 114-116 ° C; IR<br />
(KBr): 3093, 3086, 3016, 2942, 2834, 1658, 1445, 1403, 1368, 830 cm -1 ; 1 H NMR<br />
(300 MHz, CDCl 3 ): δ 1.34-1.36 (d, 6H, 2 x i prCH 3 ), 3.52 (m, 1H, i prCH), 6.67-6.73<br />
(dd, 2H, j=17.4Hz), 6.98-7.02 (d, 2H, Thiophene-H), 7.08-7.14 (t, 2H, Ar-H), 7.27-<br />
7.26 (d, 1H, Thiophene-H), 7.69-7.74 (t, 2H, Ar-H); 13 C NMR (DEPT):(75 MHz,<br />
CDCl 3 ): 21.76, 32.14, 115.35, 115.63, 120.59, 125.77, 127.23, 127.88, 130.22,<br />
132.05, 132.16; MS (m/z): 359 (M + ); Anal. Calcd for C 19 H 17 ClFN 2 S: C, 63.59; H,<br />
4.49; N, 7.81; Found: C, 63.43; H, 4.37; N, 7.70.<br />
2-Choloro-4-(4-flurophenyl)-5-[(E)-2-(furan-2-yl)vinyl]-6-isopropylpyrimidine<br />
(AW-05). White solid; R f 0.82 (8:2 hexane-EtOAc); mp 119-121 ° C; IR (KBr): 3113,<br />
2972, 1730, 1683, 1070, 881, 796, 744 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ 1.34-1.36<br />
(d, 6H, 2 x i prCH 3 ), 3.44-3.49 (m, 1H, i prCH), 6.44-6.55 (d, 2H, Furan), 6.93-6.99<br />
Department of Chemistry, <strong>Saurashtra</strong> university, Rajkot-360005 67