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Chapter 2
Synthesis of substituted pyrimidines via Wittig
4-((E)-2-(2-chloro-4-(4-fluorophenyl)-6-isopropylpyrimidin-5-yl)vinyl)-N,Ndimethylbenzenamine
(AW-11). Yellow solid; R f 0.75 (8:2 hexane-EtOAc); mp 118-
120 ° C; IR (KBr): 3092, 3028, 2966, 2823, 1660, 1428, 1368, 835, cm -1 ; MS (m/z):
396 (M + ); Anal. Calcd for C 23 H 23 ClFN 3 : C, 69.78; H, 5.86; N, 8.96; Found: C, 69.75;
H, 5.76; N, 8.77
5-((E)-(4-fluorostyryl))-2-chloro-4-(4-fluorophenyl)-6-isopropylpyrimidine (AW-
12). White solid; R f 0.73 (8:2 hexane-EtOAc); mp 54-56 ° C; IR (KBr): 3096, 3065,
2952, 2869, 1675, 1468, 1442, 1353, 836, cm -1 ; 1 H NMR (400 MHz, CDCl 3 ): δ 1.15-
1.26 (d, 6H, 2 x i prCH 3 ), 3.36-3.43 (m, 1H, i prCH), 6.35-6.39 (d, 1H, j=16.6Hz,
ethylene-H), 6.73-6.77 (dd, 1H, j=16.6Hz, ethylene-H), 6.91-7.00 (m, 4H, Ar-H), 7.21
-7.24 (m, 2H, Ar-H), 7.55-7.60 (m, 2H, Ar-H); 13 C NMR (100 MHz, CDCl 3 ): 21.72,
32.17, 115.53, 115.54, 115.80, 116.01, 121.11, 121.13, 125.99, 126.39, 128.13,
128.21, 128.49, 128.61, 132.04, 132.12,132.35, 132.39, 133.28, 133.31, 133.38,
133.41, 136.10, 150.98, 159.22, 161.62, 162.30, 164.10, 164.79, 165.66, 165.86,
177.22, 177.44; MS (m/z): 372 (M + ); Anal. Calcd for C 21 H 17 ClF 2 N 2 : C, 68.02; H,
4.62; N, 7.55; Found: C, 68.05; H, 4.66; N, 7.77
5-((E)-(3-nitrostyryl))-2-chloro-4-(4-fluorophenyl)-6-isopropylpyrimidine (AW-
13). White solid; R f 0.72 (8:2 hexane-EtOAc); mp 63-65 ° C; IR (KBr): 3130, 3083,
2932, 2856, 1652, 1428, 1426, 1375, 833, 780 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ
1.34-1.36 (d, 6H, 2 x i prCH 3 ), 3.45-3.49 (m, 1H, i prCH), 6.53-6.59 (d, 1H, j=16.5Hz,
ethylene-H), 7.08-7.15 (m, 3H, Ar-H & ethylene-H), 7.52 -7.70 (m, 4H, Ar-H), 8.14-
8.22 (s d, 2H, Ar-H); 13 C NMR (DEPT):(75 MHz, CDCl 3 ): 21.71, 32.37, 115.46,
115.75, 121.01, 123.08, 124.68, 129.95 131.97, 132.09, 132.29, 134.90; 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, 10.55
5-((E)-(4-bromostyryl))-2-chloro-4-(4-fluorophenyl)-6-isopropylpyrimidine(AW-
14). White solid; R f 0.75 (8:2 hexane-EtOAc); mp 96-98 ° C; IR (KBr): 3082, 3057,
2933, 1643, 1449, 1403, 1368, 835 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ): δ 1.23-1.25 (d,
6H, 2 x i prCH 3 ), 3.35-3.40 (m, 1H, i prCH), 6.34-6.38 (d, 1H, j=16.6Hz, ethylene-H),
6.82-6.86 (dd, 1H, j=16.6Hz, ethylene-H), 6.97-7.02 (t, 2H, Ar-H), 7.12-7.17 (d, 2H,
Ar-H), 7.37-7.39 (d, 2H, Ar-H), 7.55-7.59 (m, 2H, Ar-H); 13 C NMR (100 MHz,
Department of Chemistry, Saurashtra university, Rajkot-360005 69