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