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Chapter 1
Synthesis of functionalized pyrimidines
Spectral data for the newly prepared compounds.
Methyl 1,2-dihydro-6-isopropyl-2-oxo-4-phenylpyrimidine-5-carboxylate (ASM-
02a). White solid; R f 0.45 (1:1 hexane-EtOAc); mp 158-160 ° C; IR (KBr): 3459, 3070,
2930, 2850, 1730, 1650, 1583, 1470, 1335, 1064, 760, 700 cm -1 ; 1 H NMR (300 MHz,
CDCl 3 ): δ 1.42-1.44 (d, 6H, 2 x i prCH 3 ), 3.20-3.26 (m, 1H, i prCH), 3.57 (s, 3H,
OCH 3 ), 7.44-7.51 (m, 3H, Ar-H), 7.58-7.60 (d, 2H, Ar-H, j=6.9Hz), 12.94 (s, 1H,
OH); 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): 273 (M + ); Anal. Calcd for C 15 H 16 N 2 O 3 : C, 66.16;
H, 5.92; N, 10.29; Found: C, 66.13; H, 5.97; N, 10.27.
Methyl 4-(4-fluorophenyl)-1,2-dihydro-6-isopropyl-2-oxopyrimidine-5-carboxylate
(ASM-2e). White solid; R f 0.48 (1:1 hexane-EtOAc); mp 180-182 ° C; IR (KBr):
3470, 3093, 2999, 1735, 1648, 1586, 1450, 1261, 755, 700, cm -1 ; 1 H NMR (300 MHz,
CDCl 3 ): δ 1.14-1.16 (d, 6H, 2 x i prCH 3 ), 3.06-3.11 (m, 1H, i prCH), 3.54 (s, 3H,
OCH 3 ), 6.92-6.98 (t, 2H, Ar-H), 7.29-7.40 (d, 2H, Ar-H), 8.0 (s, 1H, NH); 13 C NMR
(DEPT):(75 MHz, CDCl 3 ): 20.82, 31.98, 52.28, 115.28, 115.56, 129.82, 129.93; MS
(m/z): 291 (M + ); Anal. Calcd for C 15 H 15 FN 2 O 3 : C, 62.06; H, 5.21; N, 9.65; Found: C,
62.13; H, 5.17; N, 9.67.
Methyl 2-chloro-4-isopropyl-6-phenylpyrimidine-5-carboxylate (ASM-03a).
White solid; R f 0.62 (8:2 hexane-EtOAc); mp 138-142 ° C; IR (KBr): 3057, 3034,
2972, 2931, 2872, 1828, 1726, 1687, 1572, 1541, 871, 767, 730, 702 cm -1 ; 1 H NMR
(300 MHz, CDCl 3 ): δ 1.32-1.35 (d, 6H, 2 x i prCH 3 ), 3.14-3.20 (m, 1H, i prCH), 3.72
(s, 3H, OCH 3 ), 7.43-7.48 (m, 3H, Ar-H), 7.65-7.67 (t, 2H, Ar-H); 13 C NMR (100
MHz, CDCl 3 ): 21.63, 33.62, 52.96, 123.49, 128.29, 128.78, 130.79, 136.37, 161.26,
166.15, 167.88, 176.53; MS (m/z): 291 (M + ); Anal. Calcd for C 15 H 15 FN 2 O 3 : C, 61.97;
H, 5.20; N, 12.19; Found: C, 61.90; H, 5.17; N, 12.27.
Methyl 2-(4-cyanophenyl)-4-isopropyl-6-phenylpyrimidine-5-carboxylate (ASM-
04a). White solid; R f 0.72 (8:2 hexane-EtOAc); mp 108-110 ° C; IR (KBr): 3194, 3154,
2976, 2929, 2290, 1722, 1683, 1456, 1300, 858, 829, 777, 698 cm -1 ; 1 H NMR (400
MHz, CDCl 3 ): δ 1.16-1.32 (d, 6H, 2 x i prCH 3 ), 3.15-3.19 (m, 1H, i prCH), 3.66 (s, 3H,
OCH 3 ), 7.39-7.42 (m, 3H, Ar-H), 7.65-7.70 (m, 4H, Ar-H), 8.61-8.63 (d, 2H, Ar-H,
j=7.8Hz); 13 C NMR (100 MHz, CDCl 3 ): 21.93, 29.69, 33.55, 52.80, 114.18,
Department of Chemistry, Saurashtra University, Rajkot-360005 27