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Pd(II)
Chapter 1
Synthesis of functionalized pyrimidines
The analytical data for ASM-04a revealed a molecular formula C 22 H 19 N 3 O 2
(m/z 358). Its 1 H NMR spectrum had signals at 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).
The proposed mechanism of the Suzuki-Miyaura coupling reaction for the
formation of C-phenyl pyrimidines is depicted in figure 35.
N
N
R
Pd (0)
N
N
Cl
N
R
N
N
Pd(II)
N
Pd(II)
Cl
HO
OCOOK
B OH
OCOOK
K 2 CO 3
HO B OH
OCOOK
HO B OH
N
N
-KCl
K 2 CO 3
KOOCO
Figure 35: Mechanism of Suzuki-Miyaura coupling reaction leading
to the formation of C-phenyl pyrimidines.
Department of Chemistry, Saurashtra University, Rajkot-360005 23