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Chapter 1
Synthesis of functionalized pyrimidines
Methyl 2-(4-fluorophenyl)-4-isopropyl-6-p-tolylpyrimidine-5-carboxylate (ASM-
04g). White solid; R f 0.73 (8:2 hexane-EtOAc); mp 117-119 ° C; IR (KBr): 3083, 2958,
1731, 1503, 1430, 1352, 1282, 1050 698 cm -1 ; MS (m/z): 365 (M + ); Anal. Calcd for
C 22 H 21 FN 2 O 2 : C, 72.51; H, 5.21; N, 7.69; Found: C, 72.56; H, 5.22; N, 7.62.
Methyl 4-isopropyl-2,6-bis(4-methoxyphenyl)pyrimidine-5-carboxylate (ASM-
04h). Yellow solid; R f 0.77 (8:2 hexane-EtOAc); mp 171-173 ° C; IR (KBr): 3028,
2924, 2868, 1729, 1523, 1480, 1430, 1268, 720 cm -1 ; MS (m/z): 392 (M + ); Anal.
Calcd for C 23 H 24 N 2 O 4 : C, 70.39; H, 6.16; N, 7.14; Found: C, 70.40; H, 6.12; N, 7.12.
Methyl 4-isopropyl-6-(3-nitrophenyl)-2-phenylpyrimidine-5-carboxylate (ASM-
04i). Yellow solid; R f 0.80 (8:2 hexane-EtOAc); mp 182-184 ° C; IR (KBr): 3056,
2967, 2850, 1735, 1505, 1480, 1320, 1252, 763 cm -1 ; MS (m/z): 378 (M + ); Anal.
Calcd for C 21 H 19 N 3 O 4 : C, 66.83; H, 5.07; N, 11.13; Found: C, 66.84; H, 5.06; N,
11.12.
Methyl 2-(4-cyanophenyl)-4-(4-fluorophenyl)-6-isopropylpyrimidine-5-carboxylate
(ASM-04j). White solid; R f 0.85 (8:2 hexane-EtOAc); mp 98-100 ° C; IR (KBr):
3058, 2931, 2858, 2235, 1725, 1522, 1492, 1268, 758, 704 cm -1 ; MS (m/z): 376 (M + );
Anal. Calcd for C 22 H 18 FN 3 O 2 : C, 70.39; H, 4.83; N, 11.19; Found: C, 70.37; H, 4.86;
N, 11.17.
Methyl 4-isopropyl-2-(4-methoxyphenyl)-6-phenylpyrimidine-5-carboxylate (AS
M-04k). White solid; R f 0.74 (8:2 hexane-EtOAc); mp 131-133 ° C; IR (KBr): 3083,
2954, 2825, 1731,1600, 1536, 1458, 1368, 1020, 738 cm -1 ; MS (m/z): 362(M + ); Anal.
Calcd for C 22 H 22 N 2 O 3 : C, 72.91; H, 6.12; N, 7.73; Found: C, 72.91; H, 6.14; N, 7.74.
Methyl 4-isopropyl-2-phenyl-6-p-tolylpyrimidine-5-carboxylate (ASM-04l).
Yellow solid; R f 0.83 (8:2 hexane-EtOAc); mp 143-145 ° C; IR (KBr): 3126, 2999,
1740, 1648, 1586, 1261, 1061, 720, 658 cm -1 ; MS (m/z): 346(M + ); Anal. Calcd for
C 22 H 22 N 2 O 2 : C, 76.28; H, 6.40; N, 8.09; Found: C, 76.29; H, 6.41; N, 8.11.
Methyl 2-(4-cyanophenyl)-4-isopropyl-6-(4-methoxyphenyl)pyrimidine-5-carboxylate
(ASM-04m). Brown solid; R f 0.72 (8:2 hexane-EtOAc); mp 177-179 ° C; IR
(KBr): 3064, 2935, 2831, 1728, 1558, 1503, 1430, 1268, 883, 778 cm -1 ; MS (m/z):
Department of Chemistry, Saurashtra University, Rajkot-360005 29