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Chapter 2
Synthesis of substituted pyrimidines via Wittig
CDCl 3 ): 21.74, 32.20, 115.38, 115.60, 121.12, 122.58, 125.80, 126.20, 127.99,
132.02, 132.05, 132.10, 133.19, 133.29, 133.32, 135.02, 136.08, 151.11, 159.34,
162.33, 164.83, 165.66, 165.87, 177.15, 177.38; MS (m/z): 431 (M + ); Anal. Calcd for
C 21 H 17 BrClF 2 N 2 : C, 58.42; H, 3.97; N, 6.49; Found: C, 58.55; H, 3.96; N, 6.47
2-((E)-2-(2-chloro-4-(4-fluorophenyl)-6-isopropylpyrimidin-5-yl)vinyl)phenol
(AW-15) White solid; R f 0.64 (8:2 hexane-EtOAc); mp 52-54 ° C; IR (KBr): 3452,
3048, 2942, 1648, 1441, 1408, 1359, 835 ,785 cm -1 ; MS (m/z): 369 (M + ); Anal. Calcd
for C 21 H 18 ClF 2 N 2 O: C, 68.38; H, 4.92; N, 7.60; Found: C, 68.35; H, 4.96; N, 7.57
5-((E)-(4-methoxystyryl))-2-chloro-4-(4-fluorophenyl)-6-isopropylpyrimidine
(AW-16). Yellow solid; R f 0.71 (8:2 hexane-EtOAc); mp 67-69 ° C; IR (KBr): 3052,
3042, 2948, 1638, 1449, 1401, 1348, 835 ,782 cm -1 ; MS (m/z): 384 (M + ); Anal. Calcd
for C 22 H 20 ClFN 2 O: C, 69.02; H, 5.27; N, 7.32; Found: C, 69.05; H, 5.26; N, 7.27
5-((E)-(2,5-dimethoxystyryl)-2-chloro-4-(4-flurophenyl)-6-isopropylpyrimidine
(AW-17). White solid; R f 0.81 (8:2 hexane-EtOAc); mp 78-80 ° C; IR (KBr): 3048,
3046, 2939, 1641, 1438, 1412, 1378, 838, 754, 779 cm -1 ; MS (m/z): 414 (M+); Anal.
Calcd for C 23 H 22 ClFN 2 O 2 : C, 66.91; H, 5.37; N, 6.78; Found: C, 66.93; H, 5.37; N,
6.75.
5-((E)-(3-bromostyryl))-2-chloro-4-(4-fluorophenyl)-6-isopropylpyrimidine (AW-
18). White solid; R f 0.78 (8:2 hexane-EtOAc); mp 87-88 ° C; IR (KBr): 3043, 3051,
2942, 1652, 1431, 1422, 1371, 831 ,786 cm -1 ; MS (m/z): 432 (M + ); Anal. Calcd for
C 21 H 17 BrClF 2 N 2 : C, 58.42; H, 3.97; N, 6.49; Found: C, 58.55; H, 3.96; N, 6.47.
5-((E)-(3-chlorostyryl))-2-chloro-4-(4-flurophenyl)-6-isopropylpyrimidine (AW-
19). Yellow solid; R f 0.73 (8:2 hexane-EtOAc); mp 50-52 ° C; IR (KBr): 3052, 3061,
2936, 1648, 1438, 1428, 1364, 838, 778 cm -1 ; MS (m/z): 373 (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.
3-((E)-2-(2-chloro-4-(4-fluorophenyl)-6-isopropylpyrimidin-5-yl)vinyl)phenol
(AW-20). White solid; R f 0.83 (8:2 hexane-EtOAc); mp 59-61 ° C; IR (KBr): 3468,
3058, 2932, 1641, 1442, 1432, 1357, 832, 781 cm -1 ; MS (m/z): 369 (M + ); Anal. Calcd
for C 21 H 18 ClF 2 N 2 O: C, 68.38; H, 4.92; N, 7.60; Found: C, 68.35; H, 4.96; N, 7.57.
Department of Chemistry, Saurashtra university, Rajkot-360005 70