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Chapter 1
Synthesis of functionalized pyrimidines
387 (M + ); Anal. Calcd for C 23 H 21 N 3 O 3 : C, 71.30; H, 5.46; N, 10.85; Found: C, 71.31;
H, 5.44; N, 10.86.
Methyl 2-(3-(dimethylamino)phenyl)-4-isopropyl-6-(3-nitrophenyl)pyrimidine-5-
carboxylate (ASM-04n). Yellow solid; R f 0.82 (8:2 hexane-EtOAc); mp 152-157 ° C;
IR (KBr): 3123, 2999, 2863,1731,1648, 1586, 1261, 1053, 850, 738, cm -1 ; MS (m/z):
420 (M + ); Anal. Calcd for C 23 H 24 N 4 O 4 : C, 65.70; H, 5.75; N, 13.33; Found: C, 65.71;
H, 5.74; N, 13.36.
Methyl 2,4-bis(4-fluorophenyl)-6-isopropylpyrimidine-5-carboxylate (ASM-04o).
White solid; R f 0.68 (8:2 hexane-EtOAc); mp 194-196 ° C; IR (KBr): 3135, 3089,
2856, 1726, 1580, 1436, 1358, 1050, 780, cm -1 ; MS (m/z): 368 (M + ); Anal. Calcd for
C 21 H 18 F 2 N 2 O 2 : C, 68.47; H, 4.93; N, 7.60; Found: C, 68.48; H, 4.94; N, 7.61.
Methyl 4-isopropyl-2,6-diphenylpyrimidine-5-carboxylate (ASM-04p). White
solid; R f 0.74 (8:2 hexane-EtOAc); mp 132-134 ° C; IR (KBr): 3120, 3025, 2868, 1745
1600, 1480, 1380, 1068, 790, 745, cm -1 ; MS (m/z): 332 (M + ); Anal. Calcd for
C 21 H 20 N 2 O 2 : C, 75.88; H, 6.06; N, 8.43; Found: C, 75.87; H, 6.06; N, 8.44.
Methyl 2-(4-cyanophenyl)-4-isopropyl-6-p-tolylpyrimidine-5-carboxylate (ASM-
04q). Yellow solid; R f 0.78 (8:2 hexane-EtOAc); mp 114-116 ° C; IR (KBr): 3051,
2967, 2850, 2253, 1725, 1568, 1503, 1430, 1268, 748, 698 cm -1 ; MS (m/z): 371 (M + );
Anal. Calcd for C 23 H 21 N 3 O 2 : C, 74.37; H, 5.70; N, 11.31; Found: C, 74.38; H, 5.71;
N, 11.34.
Methyl 2-(3-(dimethylamino)phenyl)-4-isopropyl-6-(4-methoxyphenyl)pyrimidine-5-carboxylate
(ASM-04r). White solid; R f 0.84 (8:2 hexane-EtOAc); mp 198-200
o C; IR (KBr): 3068, 2983, 2899, 1728, 1648, 1586, 1261, 1061, 780, 712 cm -1 ; 1 H
NMR (300 MHz, DMSO): δ 1.30-1.32 (d, 6H, 2 x i prCH 3 ), 2.97 (s, 6H, CH 3 ), 3.11-
3.16 (m, 1H, i prCH), 3.76-7.83 (s, 6H, OCH 3 ), 6.91-6.95 (dd, 1H, Ar-H, j=2.1Hz,
j=2.7Hz), 7.09-7.12 (d, 2H, Ar-H, j=9.0Hz), 7.32-7.37 (t, 2H, Ar-H), 7.69-7.72 (d,
2H, Ar-H, j=9.0Hz), 7.78-7.80 (d, 1H, Ar-H, j=7.8Hz); 7.86 (s, 1H, Ar-H); MS (m/z):
406 (M + ); Anal. Calcd for C 24 H 27 N 3 O 3 : C, 71.09; H, 6.71; N, 10.36; Found: C, 71.07;
H, 6.73; N, 10.37.
Department of Chemistry, Saurashtra University, Rajkot-360005 30