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Chapter 1
Synthesis of functionalized pyrimidines
The analytical data for ASM-02a revealed a molecular formula C 15 H 16 N 2 O 3
(m/z 273). The 1 H NMR spectrum revealed one doublet at δ = 1.42-1.44 ppm assigned
to isopropyl-CH 3 , a multiplet at δ = 3.20-3.26 ppm assigned to the isopropyl-CH
protons, a singlet at δ = 3.57 ppm assigned to the –OCH 3 protons, a multiplet at δ =
7.44–7.51 ppm assigned to the aromatic protons, and also a doublet at δ = 7.58–7.60
ppm (j=6.9Hz) assigned to the aromatic protons, one singlet at δ = 12.94 ppm
assigned to -OH group.
Table 1: Synthesis of substituted pyrimidines via Suzuki-Miyaura coupling.
Entry R R 1 Yield Time hrs.
ASM-04a H 4-CN 82 6.0
ASM-04b 4-CH 3 3-N(CH 3 ) 2 80 8.0
ASM-04c 4-OCH 3 4-F 87 6.5
ASM-04d 3-NO 2 4-OCH 3 92 6.0
ASM-04e 4-F H 83 7.5
ASM-04f H 3-N(CH 3 ) 2 78 8.5
ASM-04g 4-CH 3 4-F 86 7.5
ASM-04h 4-OCH 3 4-OCH 3 82 7.0
ASM-04i 3-NO 2 H 89 7.0
ASM-04j 4-F 4-CN 87 5.5
ASM-04k H 4-OCH 3 83 6.5
ASM-04l 4-CH 3 H 85 7.0
ASM-04m 4-OCH 3 4-CN 82 6.5
ASM-04n 3-NO 2 3-N(CH 3 ) 2 75 7.5
ASM-04o 4-F 4-F 80 6.0
ASM-04p H H 84 7.5
ASM-04q 4-CH 3 4-CN 89 6.0
ASM-04r 4-OCH 3 3-N(CH 3 ) 2 80 7.5
ASM-04s 3-NO 2 4-F 90 6.5
ASM-04t 4-F 4-OCH 3 86 6.0
The structures of ASM-03a was supported by its mass (m/z 291), which agrees
with its molecular formula C 15 H 15 FN 2 O 3, its 1 H NMR spectrum had signals at 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).
Department of Chemistry, Saurashtra University, Rajkot-360005 22