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Chapter 2
Synthesis of substituted pyrimidines via Wittig
Spectral data of the synthesized compounds
Methyl 2-chloro-4-(4-fluorophenyl)-6-isopropylpyrimidine-5-carboxylate (ASM-
03e). White solid; R f 0.83 (8:2 hexane-EtOAc); mp 130-132 ° C; IR (KBr): 3070, 2930,
2850, 1730, 1650, 1583, 1470, 1335, 1064, 830 cm -1 MS (m/z): 309 (M + ); Anal. Calcd
for C 15 H 14 ClFN 2 O 2 : C, 58.35; H, 4.57; N, 9.07; Found: C, 58.38; H, 4.47; N, 9.07.
(2-Chloro-4-(4-fluorophenyl)-6-isopropylpyrimidin-5-yl)methanol (INT-01).
White solid; R f 0.52 (8:2 hexane-EtOAc); mp 110-112 ° C; IR (KBr): 3459, 3327, 3193,
2999, 1648, 1586, 1261, 1061, 832 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ 1.30-1.33 (d,
6H, 2 x i prCH 3 ), 2.09 (s, 1H, OH), 3.67-3.69 (m, 1H, i prCH), 4.69 (s, 2H, CH 2 ), 7.28-
7.34 (t, 2H, Ar-H), 7.88-7.92 (t, 2H, Ar-H); 13 C NMR (DEPT):(75 MHz, CDCl 3 ):
21.40, 31.31, 56.47, 56.58, 114.99, 115.28, 131.85, 131.96; MS (m/z): 280 (M + );
Anal. Calcd for C 14 H 14 ClFN 2 O: C, 59.90; H, 5.03; N, 9.98; Found: C, 59.93; H, 5.07;
N, 9.97.
Triphenyl[2-chloro-{4-(4-flourophenyl)-6-isopropyl-pyrimidin-5-ylmethyl}-
phosphonium]bromide (INT-02). White solid; R f 0.16 (1;1 hexane-EtOAc); mp
>320 o C ; IR (KBr): 3193, 3070, 3024, 2999, 2830, 1648, 1586, 1261, 1061, 830, 780,
770, 700 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ 0.90 (s, 6H, 2 x i prCH 3 ), 2.99-3.03 (m,
1H, i prCH), 5.67 (s, 2H, CH 2 ), 6.97-7.02 (t, 2H, Ar-H), 7.26-7.33 (m, 8H, Ar-H), 7.57
(s, 6H, Ar-H), 7.75-7.80 (m, 3H, Ar-H); 13 C NMR (DEPT):(75 MHz, CDCl 3 ): 24.92,
25.53, 33.42, 116.24, 116.53, 130.35, 130.52, 131.17, 131.28, 133.97, 134.10, 135.42,
135.46; MS (m/z): 605 (M + ); Anal. Calcd for C 32 H 28 BrClFN 2 P: C, 63.43; H, 4.66; N,
4.62; Found: C, 63.45; H, 4.67; N, 5.67.
2-Choloro-4-(4-flurophenyl)-6-isopropyl-5-(E)-styrylpyrimidine (AW-01). White
solid; R f 0.75 (8:2 hexane-EtOAc); mp 80-82 ° C; IR (KBr): 3087, 3070, 3040, 2930,
2856, 1658, 1450, 1430, 1368, 830, 753, 700 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ
1.30-1.33 (d, 6H, 2 x i prCH 3 ), 3.03-3.08 (m, 1H, i prCH), 6.75-6.81 (d, 1H,
j=16.4Hz,ethylene-H), 7.04-7.23 (m, 3H, Ar-H & ethylene-H), 7.53-7.56 (d, 2H, Ar-
H), 7.72-7.74 (t, 2H, Ar-H), 8.23-8.26 (d, 2H, Ar-H); MS (m/z): 353 (M + ); Anal.
Calcd for C 21 H 18 ClFN 2 : C, 71.49; H, 5.14; N, 7.94; Found: C, 71.43; H, 5.17; N, 7.97.
Department of Chemistry, Saurashtra university, Rajkot-360005 66